New here. Please assess my situation

[DenCo]

Hello fellow mustachians.
Came across this incredibly helpful site about a month ago and spent past month studying, reading and adjusting my personal finances. I have come to realize this is what I've been striving for all my life, without knowing or fully understanding what I was doing. When I finally started reading about FIRE, it FInally REgistered... I knew I found concrete guidance.
In the past I haven't been putting too much thought into personal finances - I made enough, so why bother. as a result last year I paid $25K in taxes, while contributing only $5K to 401K. My savings were mostly in no APY savngs account not earning anything.
Since I started educating myself, I have upped my 401k contribution and looking to max it out this year, opened a high yield savings account for rainy day, highly liquid, fund.

My next steps are:
1. Pay off mortgage (I am able to borrow 50K now, once my CD matures and I am able to sell stock after holding it for 365 days I should come very close to having $145K I need).
2. HELOC for additional emergency padding. No cost, 10 year line of credit.
3. Setup investment fund outside of 401K, setup a diverse portfolio and start working towards dividend income.

My ultimate goal is leaving my corporate, soul-sucking job and working less doing something different (anything, really, preferably involving travel). I estimate to need $2K-$3K/ month. While I already have $850 in rental income, I would like to have investment portfolio providing some return and exploring options of passive income/side gigs.

I would like to get a feedback of my situation, to make sure I'm not missing anything grotesque. Sometimes outsider eyes see things I miss, so please comment and critique.
Here comes the required info:

Me = Single, 33, no dependents, US-CO, employed full-time.
Gross Salary = $6520/mo
401K = $1304/mo (+~3K annual employer contribution, which gets me to around $18K at the EOY).
HSA = $4K, +~1K annually. Don't really use it much, will look into investing the balance.
Insurance = HDHP, $90/mo
Taxes = $1504/mo
---------
Take Home = $2930/mo
Rental of my basement = $850/mo cash

Expenses (monthly):
   Mortgage = $1100 (typically overpay +$300, still owe $145K, 20 Years to maturity, 3.75%APR)
   Bills (car insurance, utilities, etc) = $500/Avg
   Groceries/Eating out = $300
   Gas = $200
   Other/Misc/Lifestyle (c0ke and h00kers. LOL) = $500
   Please note - last 3 are budgetary numbers that I don't always hit. I feel I live fairly frugal lifestyle, and I don't have the need to cut even more out. I feel my expenses are quite reasonable where they are, but this will be the first place I will be able to cut down if need comes.
   No loans other than mortgage. No outstanding debts. 

Current Savings:
Company stock ~$65K
   CD $15K
   HYSavings account $5K (rainy day fund)
   Ameritrade $300 (tried stocks, lost $200 in a year. Not proud of it)
   Vanguard 401K balance ~38K
   
Assets
   2 cars: older SUV for winter/camping, newer (~35K value) that I am looking to downgrade for savings purposes. Both paid off.

[Car Jack]

You don't mention a Roth.  Are you contributing to one? 

You're going to get people who say not to pay off your mortgage, but invest in the market instead.
You'll also get people who say to go ahead and pay off the mortgage because it's guaranteed return.

Both are right.  Do what you feel is best.

You say you've got a 401k.  Are you maxing it?  That means max before employer contribution.

You talk about dividend income outside of 401k.  That sets you up for the bad "T" word.  Taxes.  Dividends spill off and you're liable for the taxes in that year.  Let me talk to you about the opposite strategy.  Say you're in either low, or ideally no dividends.  So now, you have no dividends, the value rises and you pay no taxes.  Think stocks like BRK/b.  It follows large cap indexes like VTI, ITOT, SCHB pretty well, but you get no 1099.  Just a thought.  I've got both in my portfolio.

Have you put together a spread sheet of your investments, the ER and the cost in dollars?  When I first started getting control of my investments, I found this to be the best eye opening action I could make.  Seeing $xxx in annual fees in a column focuses you on what you're paying for.  I will admit that I'm very, very focused on cost.

[Boofinator]

There is an investment order thread which is pretty solid advice: https://forum.mrmoneymustache.com/investor-alley/investment-order/msg1333153/#msg1333153.

To summarize what I would do in your situation: Max the 401k and Traditional IRA (assuming you can fully deduct the latter) before paying off any of that debt. Any money on top of that I'd put into stocks (since you seem to have a long time before retirement).

[DenCo]

Nope, no Roth yet. Tried to open a traditional one to offset my taxes for 2018, but apparently I made too much money to write contribution off (insert cringe here). Once mortgage is out of the way, I will look into Roth as well.

Yes, I read A LOT of debates on payoff vs no-payoff. the biggest thing to me is a psychological value of having no debt hanging on me and no bank will ever come to kick me out if I can't make my mortgage payments. so I will take my guaranteed 4% return and get it over with. Plus, if I don't have my mortgage payment I can use rental income to pay almost all of my utilities, so there is self-sustainability. even in the worst of the worst case scenarios I will survive on minimum wage job putting food on my table.

Starting this year I am set to max my 401K. I didn't in the past because I didn't understand the value of it. I will have to step it up, I thought max included employer contribution. Thanks for this tip!

Since I'm just starting to seriously look into investments, I haven't started the spreadsheet, but I will look into doing it right away. Good point on the evil T of dividend income.
Is your portfolio in Vanguard? Is that where I should look into opening a personal investment portfolio too?

[MrThatsDifferent]

Definitely max your tax advantage accounts. Regarding the mortgage, I hear ya, I just would do differently. Because of your age, I’d get as much money into the market compounding as quickly as possible. You have the rent of the basement as a huge backup if you lost your job. Your worst case is then covering just $300 a month. If you have $4k in an EF, then you’re covered for a year if something goes wrong as long as you can still rent the basement. At least consider using the next 5 years to focus solely on building up your investments. Then focus the next 5 on reducing or killing your mortgage. Time is your friend and that’s what people seem to miss. You’re in a good position, make the smartest choice, not just a smart one.

[Boofinator]

Nope, no Roth yet. Tried to open a traditional one to offset my taxes for 2018, but apparently I made too much money to write contribution off (insert cringe here).

Are you sure you couldn't fully deduct your IRA? If you max out your 401k, those contributions aren't considered for IRA deduction limits, and therefore you will be very close to being able to fully deduct: https://www.irs.gov/retirement-plans/plan-participant-employee/2018-ira-contribution-and-deduction-limits-effect-of-modified-agi-on-deductible-contributions-if-you-are-covered-by-a-retirement-plan-at-work.

And I'm not sure what you mean by you "tried to open a traditional" IRA, as anybody can open one (just not everyone can deduct). Did you open one, or did you not? I'm only asking because if you did open one and found you couldn't deduct, you can always recharacterize as Roth before tax day.

[DenCo]

Sorry, to clarify IRA situation:
Last year I did not max my 401k contribution. I am just on track for it this year.

As I was doing my taxes last week and realized how much I'm getting f****ed for, I started looking at options to reduce it. I just looked at the option of standard IRA, but my MAGI was around $97K, which is higher than 73K limit when they allow you to deduct it. At this point I didn't see a reason to put my after-tax money, taxed in a fairly high tax bracket, into an IRA account. I already know in the future I will not be making this much and will not be in such a high tax bracket when I withdraw it, so to me it seemed like a loss. Maybe I'm confused and not thinking straight. I will go read more on the IRA to make sure.

[DenCo]

Definitely max your tax advantage accounts. Regarding the mortgage, I hear ya, I just would do differently. Because of your age, I’d get as much money into the market compounding as quickly as possible. You have the rent of the basement as a huge backup if you lost your job. Your worst case is then covering just $300 a month. If you have $4k in an EF, then you’re covered for a year if something goes wrong as long as you can still rent the basement. At least consider using the next 5 years to focus solely on building up your investments. Then focus the next 5 on reducing or killing your mortgage. Time is your friend and that’s what people seem to miss. You’re in a good position, make the smartest choice, not just a smart one.

Sorry, to answer this, I definitely see your point in this too. I will definitely look into first maxing 401k, then IRA, and only then mortgage. From what I understand those are the only 2 I can take before taxes, which would reduce my tax burden.

And I really appreciate all the comments... It's pretty confusing and I avoided it for years, but avoiding only means uncle Sam will take advantage of you. SO I am doing my best to educate myself now and get on the right path going forward.

[Boofinator]

Sorry, to clarify IRA situation:
Last year I did not max my 401k contribution. I am just on track for it this year.

As I was doing my taxes last week and realized how much I'm getting f****ed for, I started looking at options to reduce it. I just looked at the option of standard IRA, but my MAGI was around $97K, which is higher than 73K limit when they allow you to deduct it. At this point I didn't see a reason to put my after-tax money, taxed in a fairly high tax bracket, into an IRA account. I already know in the future I will not be making this much and will not be in such a high tax bracket when I withdraw it, so to me it seemed like a loss. Maybe I'm confused and not thinking straight. I will go read more on the IRA to make sure.

There's also the option of the Roth IRA, but for Mustachian level early retirement it really doesn't do much good (since you will likely be in a low tax bracket when you pull the money). In your case, since you have a strong desire to pay off the mortgage, I would say go for it after the 401k and HSA are maxed out. (As long as you understand it is probably the suboptimal choice for getting to FIRE as soon as possible.)

[fuzzy math]

Sorry, to clarify IRA situation:
Last year I did not max my 401k contribution. I am just on track for it this year.

As I was doing my taxes last week and realized how much I'm getting f****ed for, I started looking at options to reduce it. I just looked at the option of standard IRA, but my MAGI was around $97K, which is higher than 73K limit when they allow you to deduct it. At this point I didn't see a reason to put my after-tax money, taxed in a fairly high tax bracket, into an IRA account. I already know in the future I will not be making this much and will not be in such a high tax bracket when I withdraw it, so to me it seemed like a loss. Maybe I'm confused and not thinking straight. I will go read more on the IRA to make sure.

There's also the option of the Roth IRA, but for Mustachian level early retirement it really doesn't do much good (since you will likely be in a low tax bracket when you pull the money). In your case, since you have a strong desire to pay off the mortgage, I would say go for it after the 401k and HSA are maxed out. (As long as you understand it is probably the suboptimal choice for getting to FIRE as soon as possible.)

So in theory the OP should always be above the IRA deduction limit which would mean the Roth IRA is a great option for him specifically. The option of investing in a traditional IRA and not being able to deduct it does him no good at all.

[ysette9]

As others have said, paying off your mortgage early, and certainly prioritizing it over investing as early as possible is sub-optimized, and will result in you working longer than strictly necessary. That said, if you need to do it for emotional reasons, then the least risky way to do that is to not put any extra on the mortgage monthly but to build up a side account (maybe money market or high-yield checking, maybe a balanced investment fund with 50-60% bonds) and only pay it off in full once you have enough.

If anything happens to your ability to earn a living the mortgage company will forclose ok you just as quickly whether you owe $10k or $100k. If you lost your job and had a side account where you were saving up to lay it off in one fell swoop, at least you could slowly feed the mortgage beast from that while you look for another source of income.

By having a mostly- but not fully-paid off mortgage you retain the risk of losing the house if you can’t make the payments and you also have all of the down side risk of missed opportunity of investing.

[zee dot]

@Car Jack
You talk about dividend income outside of 401k.  That sets you up for the bad "T" word.  Taxes.  Dividends spill off and you're liable for the taxes in that year.  Let me talk to you about the opposite strategy.  Say you're in either low, or ideally no dividends.  So now, you have no dividends, the value rises and you pay no taxes.  Think stocks like BRK/b.  It follows large cap indexes like VTI, ITOT, SCHB pretty well, but you get no 1099.  Just a thought.  I've got both in my portfolio/quote]

I don't fully understand this part.
Can you please expand on this?

[DenCo]

As others have said, paying off your mortgage early, and certainly prioritizing it over investing as early as possible is sub-optimized, and will result in you working longer than strictly necessary. That said, if you need to do it for emotional reasons, then the least risky way to do that is to not put any extra on the mortgage monthly but to build up a side account (maybe money market or high-yield checking, maybe a balanced investment fund with 50-60% bonds) and only pay it off in full once you have enough.

If anything happens to your ability to earn a living the mortgage company will forclose ok you just as quickly whether you owe $10k or $100k. If you lost your job and had a side account where you were saving up to lay it off in one fell swoop, at least you could slowly feed the mortgage beast from that while you look for another source of income.

By having a mostly- but not fully-paid off mortgage you retain the risk of losing the house if you can’t make the payments and you also have all of the down side risk of missed opportunity of investing.

This is where I get a little confused. From what I understand putting 1000's into your IRA, 401k and all is a great idea, letting interest compound is also wonderful, however it's all the money I don't get to touch for the next 30 years or so. That doesn't help me retire in 10 years.
Meanwhile I am also giving the bank flushing down the toilet $500/mo in interest.
I kinda have that side account you're describing - it's my ESPP. I've been maxing out that bad boy, and it has been growing more or less steady, but stocks are volatile. I lost around $10K in December when everything took a nosedive. I go most of it back, but working in this company, I don't know how much longer they can keep doing what they're doing, so I feel like I should at the very least diversify.
I have looked at some of the Index Funds people recommend and historically I see them returning around, or somewhat more, than my mortgage interest. But there is no guarantee it won't take another nosedive, like in Dec 2018.
How realistic, and safe, is it to put that 100K into Index funds and actually see better return than the cost of paying mortgage?

[Boofinator]

Sorry, to clarify IRA situation:
Last year I did not max my 401k contribution. I am just on track for it this year.

As I was doing my taxes last week and realized how much I'm getting f****ed for, I started looking at options to reduce it. I just looked at the option of standard IRA, but my MAGI was around $97K, which is higher than 73K limit when they allow you to deduct it. At this point I didn't see a reason to put my after-tax money, taxed in a fairly high tax bracket, into an IRA account. I already know in the future I will not be making this much and will not be in such a high tax bracket when I withdraw it, so to me it seemed like a loss. Maybe I'm confused and not thinking straight. I will go read more on the IRA to make sure.

There's also the option of the Roth IRA, but for Mustachian level early retirement it really doesn't do much good (since you will likely be in a low tax bracket when you pull the money). In your case, since you have a strong desire to pay off the mortgage, I would say go for it after the 401k and HSA are maxed out. (As long as you understand it is probably the suboptimal choice for getting to FIRE as soon as possible.)

So in theory the OP should always be above the IRA deduction limit which would mean the Roth IRA is a great option for him specifically. The option of investing in a traditional IRA and not being able to deduct it does him no good at all.

I agree, no reason to invest in a Traditional IRA if you can't deduct it when Roth is available. I invest in a Roth IRA for that reason. However, I don't consider it a great option for Mustachians who are planning an early retirement, and here's why: with Roth, you pay taxes now and then aren't taxed when you pull out money; with a taxable account, you pay taxes now and then aren't taxed when you pull them out (due to long-term capital gains being 0% for Mustachian-level retirement scenarios); so essentially they are almost the same, except in taxable you get taxed on dividends while you are working (maybe 2% dividends x 15% tax = 0.3% drag), but you also get to do tax loss harvesting (which saves maybe $750 per year). So for a brand new Mustachian investor, I don't see Roth as a great investment.

[ItsALongStory]

You keep saying you are making 401k but data doesn't seem to show it. The IRS limit for 2019 is 19k for your own contributions, this does not include your match. There are also taxable contribution options but those should be lower on the list.

Sent from my Pixel 2 XL using Tapatalk

[Boofinator]

As others have said, paying off your mortgage early, and certainly prioritizing it over investing as early as possible is sub-optimized, and will result in you working longer than strictly necessary. That said, if you need to do it for emotional reasons, then the least risky way to do that is to not put any extra on the mortgage monthly but to build up a side account (maybe money market or high-yield checking, maybe a balanced investment fund with 50-60% bonds) and only pay it off in full once you have enough.

If anything happens to your ability to earn a living the mortgage company will forclose ok you just as quickly whether you owe $10k or $100k. If you lost your job and had a side account where you were saving up to lay it off in one fell swoop, at least you could slowly feed the mortgage beast from that while you look for another source of income.

By having a mostly- but not fully-paid off mortgage you retain the risk of losing the house if you can’t make the payments and you also have all of the down side risk of missed opportunity of investing.

This is where I get a little confused. From what I understand putting 1000's into your IRA, 401k and all is a great idea, letting interest compound is also wonderful, however it's all the money I don't get to touch for the next 30 years or so. That doesn't help me retire in 10 years.
Meanwhile I am also giving the bank flushing down the toilet $500/mo in interest.
I kinda have that side account you're describing - it's my ESPP. I've been maxing out that bad boy, and it has been growing more or less steady, but stocks are volatile. I lost around $10K in December when everything took a nosedive. I go most of it back, but working in this company, I don't know how much longer they can keep doing what they're doing, so I feel like I should at the very least diversify.
I have looked at some of the Index Funds people recommend and historically I see them returning around, or somewhat more, than my mortgage interest. But there is no guarantee it won't take another nosedive, like in Dec 2018.
How realistic, and safe, is it to put that 100K into Index funds and actually see better return than the cost of paying mortgage?

Tax-deferred assets would help you retire in 10 years. There are several ways to get the money out essentially tax-free: look into SEPP or, if you'd like more control (but a bit more work), you could do a Roth conversion ladder. Each of these has pros and cons, but either would help you in reaching your retirement goals.

[doggyfizzle]

You talk about dividend income outside of 401k.  That sets you up for the bad "T" word.  Taxes.  Dividends spill off and you're liable for the taxes in that year.  Let me talk to you about the opposite strategy.  Say you're in either low, or ideally no dividends.  So now, you have no dividends, the value rises and you pay no taxes.  Think stocks like BRK/b.  It follows large cap indexes like VTI, ITOT, SCHB pretty well, but you get no 1099.  Just a thought.  I've got both in my portfolio.

Well, for ER purposes, dividends (QDI) are actually a pretty tax-efficient form of income.  If OP stays single, as long his his AGI is below $38.6k his QDI rate is 0%.  That number is greater than his current expenses, so some dividend income from a diverse basket of equities (or m-fund like VWINX) could supplement his rental income from the basement so he wouldn’t have to pull money from a 401k or IRA.

[ysette9]

As others have said, paying off your mortgage early, and certainly prioritizing it over investing as early as possible is sub-optimized, and will result in you working longer than strictly necessary. That said, if you need to do it for emotional reasons, then the least risky way to do that is to not put any extra on the mortgage monthly but to build up a side account (maybe money market or high-yield checking, maybe a balanced investment fund with 50-60% bonds) and only pay it off in full once you have enough.

If anything happens to your ability to earn a living the mortgage company will forclose ok you just as quickly whether you owe $10k or $100k. If you lost your job and had a side account where you were saving up to lay it off in one fell swoop, at least you could slowly feed the mortgage beast from that while you look for another source of income.

By having a mostly- but not fully-paid off mortgage you retain the risk of losing the house if you can’t make the payments and you also have all of the down side risk of missed opportunity of investing.

This is where I get a little confused. From what I understand putting 1000's into your IRA, 401k and all is a great idea, letting interest compound is also wonderful, however it's all the money I don't get to touch for the next 30 years or so. That doesn't help me retire in 10 years.
Meanwhile I am also giving the bank flushing down the toilet $500/mo in interest.
I kinda have that side account you're describing - it's my ESPP. I've been maxing out that bad boy, and it has been growing more or less steady, but stocks are volatile. I lost around $10K in December when everything took a nosedive. I go most of it back, but working in this company, I don't know how much longer they can keep doing what they're doing, so I feel like I should at the very least diversify.
I have looked at some of the Index Funds people recommend and historically I see them returning around, or somewhat more, than my mortgage interest. But there is no guarantee it won't take another nosedive, like in Dec 2018.
How realistic, and safe, is it to put that 100K into Index funds and actually see better return than the cost of paying mortgage?

I think it would be educational for you to head over to the Don’t pay off your mortgage early thread and read up on the debate about paying it off early versus not. It depends on your timeframe. If you are telling about the next year or two, then yes, the stock market is a risky place to be and you would be better off taking a guarantee return of paying off a low interest mortgage. But once you are talking about ten or fifteen or twenty years, then historically the stock market has pretty much always had a positive return and on average much better than your mortgage interest rate. Other people have looked at the details and can speak to them much better than me.

Your ESPP is a great way to get stock at 10% off, or whatever your specific setup is, but it is very risky in that it is a single stock.
I hope you are selling it as quickly as possible and moving those funds into something more diversified.

Instead of just focusing on the money you are paying in interest you have to also think about the opportunity cost of your money. There are always lots of choices of what to do with it and the goal is to pick the best, not just one that is not bad. Paying off a mortgage early is solidly a not-bad choice. Way better than blowing it on hookers and booze. But there are better choices out there if we are taking about the long-term picture. That is what I am trying to say.

There are several ways of accessing funds from retirement accounts early. You can read hi on them here. https://forum.mrmoneymustache.com/investor-alley/how-to-withdraw-funds-from-your-ira-and-401k-without-penalty-before-age-59-5/

[BrightFIRE]

This is where I get a little confused. From what I understand putting 1000's into your IRA, 401k and all is a great idea, letting interest compound is also wonderful, however it's all the money I don't get to touch for the next 30 years or so. That doesn't help me retire in 10 years.
Meanwhile I am also giving the bank flushing down the toilet $500/mo in interest.
I kinda have that side account you're describing - it's my ESPP. I've been maxing out that bad boy, and it has been growing more or less steady, but stocks are volatile. I lost around $10K in December when everything took a nosedive. I go most of it back, but working in this company, I don't know how much longer they can keep doing what they're doing, so I feel like I should at the very least diversify.
I have looked at some of the Index Funds people recommend and historically I see them returning around, or somewhat more, than my mortgage interest. But there is no guarantee it won't take another nosedive, like in Dec 2018.
How realistic, and safe, is it to put that 100K into Index funds and actually see better return than the cost of paying mortgage?

You can get your money before you turn 59. You need to read this (and his whole site has lots of great data on how tax-sheltered growth works) https://www.madfientist.com/how-to-access-retirement-funds-early/

You didn't lose $10k unless you sold. However, I think most folks agree that you should't have all your money in your employer - lots of them turn around and sell the stock ASAP before they have any gains to pay and then take that money and reinvest it in an index fund.

If it isn't realistic or safe to put money in an index fund we're all hosed. :-) You don't seem like you fully understand your options. Also check out the Simple Path to Wealth/How to Invest series https://jlcollinsnh.com/stock-series/

[DenCo]

This is where I get a little confused. From what I understand putting 1000's into your IRA, 401k and all is a great idea, letting interest compound is also wonderful, however it's all the money I don't get to touch for the next 30 years or so. That doesn't help me retire in 10 years.
Meanwhile I am also giving the bank flushing down the toilet $500/mo in interest.
I kinda have that side account you're describing - it's my ESPP. I've been maxing out that bad boy, and it has been growing more or less steady, but stocks are volatile. I lost around $10K in December when everything took a nosedive. I go most of it back, but working in this company, I don't know how much longer they can keep doing what they're doing, so I feel like I should at the very least diversify.
I have looked at some of the Index Funds people recommend and historically I see them returning around, or somewhat more, than my mortgage interest. But there is no guarantee it won't take another nosedive, like in Dec 2018.
How realistic, and safe, is it to put that 100K into Index funds and actually see better return than the cost of paying mortgage?

You can get your money before you turn 59. You need to read this (and his whole site has lots of great data on how tax-sheltered growth works) https://www.madfientist.com/how-to-access-retirement-funds-early/

You didn't lose $10k unless you sold. However, I think most folks agree that you should't have all your money in your employer - lots of them turn around and sell the stock ASAP before they have any gains to pay and then take that money and reinvest it in an index fund.

If it isn't realistic or safe to put money in an index fund we're all hosed. :-) You don't seem like you fully understand your options. Also check out the Simple Path to Wealth/How to Invest series https://jlcollinsnh.com/stock-series/

You're right I don't fully understand them. The more I read, the more confusing it gets too. LOL
I already have the JLCollinsNH tab open and going through the articles.
I agree that keeping all my money in employer ESPP wasn't the best idea, but it worked ok in terms of gains and I am starting to sell the stock now (I will owe a small fortune in taxes this year, but oh well - lessons learned, money earned).
I read multiple "don't pay off your mortgage" threads. It's not that I don't understand that side of the argument. Investing $100K instead of covering the debt is counter intuitive to me. I believe one of the articles linked/read talked about it being the natural desire to get rid of the debt. And I see many other saying that money borrowed at 3.875% is "cheap" and the cash is better invested elsewhere.
So I continue to do my homework (and becoming an economist in process). and I appreciate everyone who contributed here!

[DenCo]

OK, after a long weekend of reading and studying I changed my mind and instead came up with the new plan. I will hold off on paying off the mortgage and instead invest the money. I do need some advice on this, which I will put here rather than opening a new thread.
1. I will max out my 2018 HSA (this will reduce my tax burden for last year)
2. I will have ~50K of after-tax cash to invest. Although this has already been taxed at a pretty high rate, I understand it's still advantageous to first max out Roth (max for 2018 $5500) and the rest into regular taxable account, which I will open with Vanguard (seems to be popular choice and my 401K is already there).
3. I hope to bring my MAGI for 2019 low enough to allow traditional IRA deduction, but I will wait until later in the year to be sure of that before I invest into traditional. If not, I can always put money into Roth end of 2019/early 2020.
4. For 2019 my 401K and HSA will be maxed out through payroll deduction.
5. I will continue to pay mortgage + $200-$300 to pay down principal faster and contribute any additional earnings (if any) into my taxable investment account.
6. Look into further cutting monthly expenses. the usual everyday struggle...

Anyone see an issue with this?

[Linea_Norway]

Sell the second car.

If you need a car that can drive in the winter and that you can use for camping and that is more economic than your current SUV, then buy a normal, fuel efficient car, with 4x4. Maybe a station car if you want to sleep in the car itself. To me it is a bit silly to have a second car just for winter purposes. Here in Norway everyone drives the same car in summer and in winter, we all just swap tires twice a year. People with 4x4 drive much more easily on hills in the winter than those without 4x4. But you don't need to have a clumpy, uneconomic SUV to drive a car with 4x4.

So my idea: swap both cars for 1 economic car that can cover all your needs.

[Boofinator]

OK, after a long weekend of reading and studying I changed my mind and instead came up with the new plan. I will hold off on paying off the mortgage and instead invest the money. I do need some advice on this, which I will put here rather than opening a new thread.
1. I will max out my 2018 HSA (this will reduce my tax burden for last year)
2. I will have ~50K of after-tax cash to invest. Although this has already been taxed at a pretty high rate, I understand it's still advantageous to first max out Roth (max for 2018 $5500) and the rest into regular taxable account, which I will open with Vanguard (seems to be popular choice and my 401K is already there).
3. I hope to bring my MAGI for 2019 low enough to allow traditional IRA deduction, but I will wait until later in the year to be sure of that before I invest into traditional. If not, I can always put money into Roth end of 2019/early 2020.
4. For 2019 my 401K and HSA will be maxed out through payroll deduction.
5. I will continue to pay mortgage + $200-$300 to pay down principal faster and contribute any additional earnings (if any) into my taxable investment account.
6. Look into further cutting monthly expenses. the usual everyday struggle...

Anyone see an issue with this?

Looks like a solid plan. Just keep in mind the stock market goes through gyrations, so you will want to develop an asset allocation plan for your investments and be prepared to stick with it.

Also, one small thing I might do differently, if only for psychological reasons: You talk about lump-summing a large amount of cash into the market in your taxable account (~45k after Roth), and then down the road putting extra down on the mortgage. I would probably reverse these two, only because lump-summing into the market a large amount (starting from $0) could be psychologically bruising if the market takes a quick dump. So instead, I might put half to 3/4 of that lump sum into the mortgage and the rest in a taxable account, and then putting all extra money going forward into your taxable account (rather than the 200-300 going into your mortgage). The only reason for doing it this way, I should stress, is to make sure future you sticks to your plan despite any ups and downs of the stock market.