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it's not usually a good idea to buy a house as an investment. buy a house because you want the house, not for an investment. your money will make more money invested somewhere other than a house. additionally, based on talking about renting rooms to pay the mortgage and the gi bill, i assume you are planning on going to school and not working? i am not that familiar with va loans, but i imagine they will require you show some form of income before they are willing to give you a loan. 14% returns over the long run are very good, but last year the market was up almost 30%, if you were only at 14% for last year you left quite a bit on the table. i would advise against  individual stocks for investments except as a hobby. put the majority of your investments into etf's/low fee mutual funds and keep a smaller amount that you can afford to lose in stocks.
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