Re: First Boat Buying Advice
Capri 18 is probably trailer-sailable, but borderline stiff enough for larger waters.
Capri 22 is also trailer-sailable (I've done it solo), setup time is about 1 hour... It'd be a lot of work, but the wing keel model is launchable at a decent ramp without drowning the truck, default newer config is an extendable tongue, the tilting trailer on the older models doesn't really help launch it.
These are big for trailerables... and the 22 is a decent performer PHRF 210 without spin. 204 with spin. the Capri 18 is a slug, but smaller, and easier to solo launch.
The S2 7.9 is a great boat, but day sailing it from trailer would be a struggle. I wouldn't recommend my Capri 25, or a J/22 or 24 for the same reasons.
Other considerations... Hunter 23... Precision 21... (Precision 18, but might be too light for larger waters).
Compac 19 or 23... the 19 is doable as a trailer day sail, the 23 probably a lot harder, both are not real sporty.
If you hit the lottery, the Left Coast Dart is an option (I'm trying Jim Lee, hey someone will take you up on it - and I can live vicariously)...
Hull #68 S2 7.9 on our little landlocked puddle, Lake Wallenpaupack, PA, it's cheap, trailerable, and paid for.