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I do not see enough thoughts on retirement plans and your at the prime age to start, especially if you want to retire young if you want to. Plus your almost throwing away money by not investing into your retirement funds. So where are your contributions to your SEP IRA? You could do some catch up contributions btw.
Will your roommate situation cover most or all of your own rent so your still living free or almost free?
Is your 150k liquid? If so why?
What kind of rent do you get for your rental? Vacancy rate? Month to month or lease? How is property tax, any maintinance fee's? Give rental details.
Why college and not just a trade school into a blooming field like green technology or even just some computer certification? What would you take in school to fall back on?
Why plan on selling any unit in 5 years? Odds are the market would just starting to turn around but good chance they would not. Plus why sell real estate? You can use additional houses like piggy banks if your careful about it. Plus you would not have built up that much equity unless you put a shitload down. Oh is your first one paid off?
Anyways I would never sell them unless you have to. If needed just borrow against them and keep them rented out. They are assets.
Do not just fancy up your house either. Understand appraising first. Just do upgrades that will get you most or a good chunk of your money back in value added to your house. Stay away from the ones that do not provide value, unless you have too.
Also would keep your vehicle super cheap.
I could really go on and on but your info is not only lacking, you are on what seems like the right path but really isnt.
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