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I'll reiterate the "go for it" sentiments previously expressed. I wish I had gone with my instincts 30 years ago and bought a boat to live on........

As for what kind of boat to look for, you can get a lot of bang for your buck with older boats, and the old Morgan OI 33 is a great example of something within your price range that would make a very comfortable live-aboard (I have no connection to the seller of this boat, by the way):

1979 Morgan 33 Out Island Sail Boat For Sale - www.yachtworld.com

Good luck with your quest, and keep us in the loop on what you decide to do.
 
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