I would suggest a Catalina 22ft for that
many people. Very popular boat. I had
an 1983 model. Well made, easy to
work on, easy to sell when you move
up. I had the retractable keel but never
had a trailer(was in a slip) Your ballast
is in the keel, it weighs something like
800 lbs and hangs down 4.5 feet or so.
Stable, easy to sail, popular for racing
fleets too. A 5hp Nissan motor pushed
it very well. I suggest rigging all the
sails to be able to be raised and lowered
from the cockpit. Makes things easier.
Rob