I can only speak for the Catalina 22 'poptop' with a swin keel.
I had the UK version and liked it, sailed it offshore, island hopped around Scotlands West coast and trialed it down to the Adriatic from the UK.
I liked the extra room the poptop gave. It had LOTS of storage space. It sailed fairly well although I believe there is a tall mast option for light air sailors. I had an 8hp OB.
IMHO that size of boat is about the max you should consider if you plan to trail any distance with your current vehicle.
Get one that has a 4 wheel trailor if you can.