If you're looking used, one to consider is a Hobie-18 with the magnum or SX "wings". You can single hand an 18 up to decent wind conditions - the furling jib gives you options in sail plan on the fly. I've single-handed mine in up to low 20's but I weigh 200+. The wings give you extra leverage for trapping single-handed, and also give real estate for bring along extra friends. I've sailed with four adults - you won't win speed records but it's decent fun. Another good thing about the wings is that if you are squeamish about trapezing, you don't have to - hiking from the wings gives almost (but not quite) the righting moment of trapping from the hulls.



Downside - the boat is a bit heavy, it takes a little muscle/creativity to move it around by myself, but I have. It may also require careful planning for the event you may need to right it by yourself, but this will be an issue for any boat you want for multi-purpose.



The best thing about this option is that the boats are fairly available and affordable on the used and new market. They're pretty robust as well. Maybe not the best option for racing, but certainly a great alternative for what you are looking for.