Good Financial Plan?

[Jeffage]

Ok...I'm sorry for the lack of detail, but here goes. I live in the Washington, DC area and have a decent job (40's), but make more money playing poker on the side than working. I like my job, but I'm not sure how long I want to stay in the area, and what I really want to do ultimately. I've rented for 3 years here and currently pay $1000 a month in rent. Condos in any place I'd want to live (near metro, cool area, etc) are in the 300k range for a one bedroom. While the market is great here, I don't know how much it can keep going up and up...is it worth locking up a ton of money to buy or better to just put it in mutuals or whatever? Having a huge mortgage payment would scare me (though I have a good cash reserve), but I could swing 25k for a down payment. Also, if I'm not sure I'll be here for say, 5 years, is it worth buying?

Other option is to continue to rent here as long as I stay here, but buy a place in Atlantic City as both a vacation home/investment property. I'm there twice a month anyway and spend like 300 on hotels, plus the town is totally reinventing itself (cleaning up the ghetto, shopping, etc). I could also rent it in August for money towards the mortgage. And it would allow me to spend more time in AC which would lead to more poker profit. Thoughts? One bedrooms on the boardwalk can be found for like 150.

Jeff