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Try to narrow down your list and then look for owner groups. You might find an owner in the owners group that lives within a drive of you. Hit them up for a visit, I'll bet they bite. I did that a few times. The hardest part was finding specific boats locally.

If your wife is going to be a part of this deal, she has to be comfortable, and that usually means a bigger boat.
Our first boat was a 21'er, a year later we were in a 26'er. That cost us. I'd suggest you take a LOT of time on each boat in question thinking about how you would live on it for any period of time. You might be happy with a sun shower but she might not. Is there space enough for clothes, pots n pans, food, beverages, life jackets, etc etc???
Longer waterline will generally give a more comfortable ride. You might like the excitement of getting tossed around but will she?
I say you buy the biggest boat you can be comfortable affording. The cost of buying up in a few years will eat your savings in buying a too short a boat. She can hang out in the marina while you crew on a race boat occasionally.
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