I just erased my lengthy response by accident and I don't have time to retype the whole thing allow me to sum up.
Consider head room, size of the head, draft and weight. A roller furler is nice to have and can be trailered no problem. Pick up a copy of The Complete Trailer Sailor by Brian Gilbert, or something like it. He has tons of great information on the topic but more importantly he includes about 50 or so boat in the 16'-26' range in the back. Specs, photos, drawings, pros and cons. It can help you pick the perfect boat for you.
Gotta go! Ebeneezer is calling!
Fair Winds and fairer deals,