It depends on what you're looking for - Performance? Accomodations? Daysailing or overnighting?
I've owned 3 different trailerables over the last 7-8 years . . .
Laser - fast, fun, wet, single sailor boat. Tiny dry storage for your wallet/keys. Boat/trailer weigh < 1000 pounds. Unobstructed view in the mirror as it's too short to see behind the tailgate of the truck; no tongue extension necessary. 15 minutes to set up. No danger of falling off while on the trailer because you should be on the boat if it's on the trailer.
Catalina 16.5 - fast, fun, sometimes wet, 3 adults or 2 adults and 2 kids. Huge cuddy for storage only. Boat/trailer weigh about 1000-1500 pounds; no tongue extension necessary. Blocks view in the mirror so you must use wing mirrors. 30-45 minutes to set up. Fell off boat on trailer once, tucked & rolled, scrapes, no major injuries.
Catalina Capri 22 fin keel, tall rig; wing keel and standard rig options available - Fast, fun, rarely wet. Large cockpit comfortably seats 4 -5 adults if it's not blowing like stink. Cabin with v-berth and 2 quarter berths, optional potty & alcohol stove. Faster (more sail area, more performance oriented hull design) than the venerable Catalina 22 but no pop top for added headroom. Weighs about 3500 pounds with the trailer; tongue extension or strap launch setup necessary. Fin keel puts hull mostly above line of sight so good view in mirror; probably not true for the wing keel. 2-3 hours to set up at start of season, less for mid-season trips where you don't have to tear everything apart (e.g. leave main on boom & store in cabin), don't remove cushions, life jackets, stove, etc. Fall from deck while on trailer could result in broken bones or death.
One of our slip neighbors has an older Catalina 25. Nice cruiser with headroom (and pop top), galley, potty, dinette, etc. Sail area and performance are comparable to my Capri 22 - I seem to be faster on some points of sail, he's faster on others. Weight on the trailer about 5500-6000 pounds, tongue extension or straps necessary for launch. Unsure as to view in the mirror. Set up time and fall from deck while on trailer similar to Capri 22.
Any of these boats can be found within your price range so the question is, what features do you want/need where you sail? Shallow water or deep? Fin, wing or swing keel or maybe a centerboard? Overnighting or just day sailing? Do you want to race or cruise? What will you tow with? Will it handle the weight of boat/trailer?
Details, man, details! 8^D
Chris
