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I would begin by thinking about what features you want on your boat.
Do you want to sleep on it?
Cook on it?
Porta-potti?
Do you want a motor on it?
Do you want to swim off of it?
Fish from it?
Race it?
How far might you trailer?
You can do all of that on njking's boat. A Macgregor 26 (which I have sailed for 15 years) is also an option and you might find an older one cheap.
I prefer a trailerable that sits low on the trailer which means no fixed keel boats. The higher the boat sits, the further down a ramp you must back to get the boat to float off the trailer.
I like 15" wheels for trailering long distances.
If the kids and I swim from the boat, I want something stable for reboarding.
You get the idea.
There are lots of great boats that fit all kinds of needs.
You might check out the "Trailer Sailor" organization. They have a monthly newsletter with stories by members and classifieds. Google it.
Good luck
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