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Should I go safe or be more aggressive?
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Don't invest in something that you don't know or don't have the time to research (pure stocks as you pointed out), but be aggressive! The younger you are the more aggressive you should be and you're about as young as they come for retirement investment advice. The reason is that your time horizon is so huge that you can weather losses and recoup them down the line, so the risk of an aggressive plan isn't quite as risky to you. It's like starting a business when you're young as opposed to starting it when you're old. So find yourself an aggressive mutual fund to invest in. Also, if you want to, you could invest in a "simple" stock or two. For example, I would consider Berkshire Hathoway to be similar to a mutual fund that's run by Warren Buffet. You should be able to put money in there and forget about it until Buffet's health starts fading significantly.
Lastly, I know that you mentioned you're maxing out your Roth at the $5k / year limit, and you've got your military retirement pay coming. I'm not familiar with the military retirement package. Do you have any other tax-deferable vehicles open to you, such as a 401k, optional pension plan, etc.? I believe that's what the poster above me was talking about. Take advantage of all of these before you start playing with money in a taxable account. Also, if you have the option to put money into a TASC account - again I don't know what military options are - I would put as much in as you're comfortable with spending this year. Anything put in there immediately "earns" you whatever your tax rate is so long as you don't let it go to waste.
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