There are always plenty of different opinions about keel types, but if you're planning to actually keep the boat on a trailer when you're not sailing it, you may want to give the swing keelers another chance. That shallow draft with the keel up makes it a lot easier to launch and haul.
There are all kinds of boats in that size range, but some of them will be pushing the limit of relatively feasible trailerability, so sticking to the smaller/lighter boats in the range might help.
The Catalina 22 is one of the most common, and with the pop-top cabin, can be moderately comfortable for spending a few days aboard. There are plenty of others; you might try a forum search for "trailer sailor" or "trailerable".
Carolina Wind Yachting Center, Washington, NC
Charters * Brokerage * Pacific Seacraft * Zodiac
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Who is staring at the sea is already sailing a little.