Hey YoungStache,
I too recently found MMM, but alas I am a bit older (34). I have been interested in saving and investing since I was 16. If I were you, this is what I would do:
1- NEVER sell your condo (unless prices absolutely skyrocket)!!! Of course you should do the math and see what kind of return you would get for renting it out. It seems like it is in a prime location within walking distance to businesses that pay VERY good salaries. You should be set up to make a decent return on that investment. MMM has some good articles on how to calculate if it will be a money maker. I've been a landlord before, and the key is to get the right tenant. Make your condo your first rental property, get a handle on what you need to do, then see about buying more property if it suits you.
2- After you reach your max matching contributions from your employer put all of your savings into a regular investment account. If you are going to be FI at a very young age you may need to withdraw from your Stash at some point. It is much easier to do that from a non-retirement type account (too many rules for retirement accounts). MMM suggests low cost index funds from Vangaurd, any large firm competes pretty well on the cost of index funds nowadays. Leave your "retirement" type accounts alone until you reach at least 59.5yo, then you can withdraw from them however you want. By then your retirement accounts should be hundreds of thousands of dollars simply by putting the minimum in to get the match. Just to calculate based on your current scenario - you are putting in ~$7500 per year (including match). If that stays the same for 10 years (FI at 10 years from now!!) at 7% annual return, that would equal ~$125,000. At that time you will quit working, and thus quit contributing to your "retirement" accounts. But you aren't going to withdraw from them until you reach 59.5yo. If you are 22 now, you would be FI at 32, and your retirement accounts would continue to compound for another 28 years. That means they will keep growing at 7% per year until then which would equal ~$831,000. This scenario is based on only putting in $7500 for 10 years from age 22-32. So, you really don't have to put very much money into your "retirement" accounts for it to compound into a sweet nest egg. Put any extra money into a regular investment account.
Best regards,
DrFunk
Not good info on the bolded part. Best way to fill your "buckets" is employer-sponsored up to the match, HSA (if you have one), then Roth IRA if eligible, then back to max out the employer-sponsored (if it is pre-tax), then taxable if there is anything left over. Some of that may be subjective, but the taxable account should be filled last.
The pre-tax "retirement" accounts are a two-fold win - you're getting more of your money to invest (since it's not losing a portion to tax) and you're reducing your taxable income by whatever your contribution is, and that may mean much less taxes owed during your working years. So even if you're not getting a match and yes, even if you have crappy investment choices available, if it's pre-tax it probably is still a good idea to max those accounts (and roll them after you leave the job into an IRA so you can change your investments to much better choices)
It is absolutely possible to access traditional/Roth/401K before the age limit of 59 with no penalties, and maxing out your pre-tax vehicles
before using a taxable is usually the best move for early retirement that I've seen. SEPP/72 t is one method, Roth Pipeline/Ladder is another. Do research these options (and check out MadFIentist's blog as well for details).
OP, it sounds like you're not really that excited about investing and managing rental property. While it is a great way to make income, you really need to do your homework on all of the responsibilities. There is a real estate investing section in this forum, but I've heard the real estate gurus also recommend the site biggerpockets.com as well for info. Don't go into buying a place without knowing the ROI, 1% rule, how to find good renters and deal with the vacancy factor, and feel competent to manage and maintain the properties - you'll be on the hook when the toilet backs up or the dishwasher goes out or the place needs a new roof!
I personally am not interested in the least in rentals as an investment due to all the hassles (wish I was, as I'm in a low cost of living/high return area) and plan on using regular investments to fund my early retirement.
You should totally do a Roth IRA. It is after tax money, but it grows tax free and you can always take out your contributions at any time penalty free. And it is a vital component for the Roth pipeline method of early retirement withdrawals... which if you do correctly means you could be paying no taxes in early retirement at all!
http://www.madfientist.com/traditional-ira-vs-roth-ira/http://www.gocurrycracker.com/never-pay-taxes-again/http://jlcollinsnh.com/2012/05/30/stocks-part-viii-the-401k-403b-ira-roth-buckets/