50k or less, 35-38ft, great sailing quick boat
I'm not sure of how much experience you have with maintenance, but reading your post, the first thing that comes to mind is that witha 50K budget you should be looking at smaller boats.
Unlike an apartment, when a problem occurs on a boat, it usually needs to be dealt with pretty quickly. Problems get fairly costly when you are dealing with a 38 footer...usually in the thousands rather than the hundreds of dollars.
Really well-maintained newer 36 or 38 foot boats usually cost more than you have available to spend. I think you'd be doing your self a favor looking at shorter, newer craft.