Thanks for the additional info, very helpful. So really, you have $82k in income, and about $51k in expenses (some of which are deductible business expenses) - do you see how that is a completely different financial picture from $29k income and $28k expenses?
Immediate recommendation: switch that Roth to a traditional IRA. The reason to do a Roth is when you think your future taxes will be higher than your current taxes. You currently have
@$60k income (not counting rentals) and will be living on less than half that when you FIRE, so a Roth makes no sense at all. That and the HSA will knock your taxable income down to
@$39k (again without considering rentals), which will knock that tax bill down significantly.
Second: ITA, you should ditch the first house immediately. Even if you walk away with nothing, you are
still up $6k/yr. Every year from here on out. Or to look at it another way: that $6k you are covering every year is $150k more you need in your ‘stache before you can RE, just for the privilege of hanging onto an asset that is bringing you no joy or utility whatsoever.
Third: I strongly recommend you hire a CPA this year to make sure you are managing the taxes appropriately for your rental properties, meaning taking all of the deductions that are available to you and helping to figure out how the new tax law will affect your situation. You have a lot of balls in the air, and I am not remotely competent to run you through the financial implications of all of them.
More generally, ditching the bad rental is going to help quite a bit, because now you can use that $5k/yr profit from the good rental towards your post-FIRE income needs. Assuming your RE budget is around $30k/yr (because you will need to pay health insurance premiums, which are not in your current $28k figure), that leaves you a delta of $25k/yr to cover. Per the 4% rule, that suggests a ‘stache of about $625k.
The other option to consider is selling both the bad rental and your current home and moving back into the good rental. Your housing costs for your current place are
over half of your expenses ($15k between mortgage, condo fees, maintenance, insurance, taxes, and electric). Looks like you can cut that by $8-9k by moving back into the old place, where you have no mortgage (and which I assume is smaller and so likely cheaper to insure/provide power to).
Obviously, do the math yourself here on decreased expenses vs loss of rental income, and this is also something to talk over with your CPA — the best way to really feel like you know what you need to do is to run the math yourself with different scenarios and see which leaves you better-off in the end. Also consider refinancing whatever property(ies) you decide to keep to a 30-year — your multiple 15-yr mortgages are causing a cash-flow squeeze and artificially inflating what you need to FIRE. I could understand pushing the 15-yr if that’s going to allow you to pay off the mortgage by the time you FIRE (that’s what we did), but you are going to be carrying these for years post-FIRE. And worse, it jacks up your budget in your early FIRE years, when you will be covering 100% of your needs from your ‘stache, and before you get any help from SS! So you will have double-luxury in your 60s and on (no mortgage +SS), but will either be super-tight from 40-62, or will have to work extra years to meet that initial income need. Plus rates are still near historic lows, so you can still get a very good 30-yr rate (and the interest is a total least deductible if you itemize).
Finally, you may benefit from the “bucket” approach that I picked up here: divide your post-RE years into different periods based on anticipated changes in your income/expenses. So for ex from 40-52, your expenses would include your mortgage; from 52-62 (or 67, or 70, or whatever) it is your expenses without mortgage; then at whatever time you plan to claim SS, you would add that into your income stream (meaning that there is less your own ‘stache needs to cover); etc. You start with the furthest-out period and multiply the annual amount you need to meet your income gap by the number of years in that period, then you present-value that back to total - that tells you how much of you’re current ‘stache you need to cover that last period of your life. Then you do the same with the next period, and the next, present — that will then tell you how much of a gap you really need to fill. FWIW, I found this approach gave me a pretty significantly lower figure than the 4% rule (which doesn’t really account well for things like “I will get SS, but not for another 25 years”).