I've kind of started looking closely at Montgomery's and Catalina 22s. I kind of shied away from Catalina's in bigger boats cause there seemed to be much more selection on the market and they are hard to re sale in the sf bay area. In the smaller boats they seem to be a good choice though.
If you want the family sailing support of an active association, check out the larger Potter designs like the 19, or give in and "be assimilated" by the Catalina 22 families.
If there were more examples to choose from in your area, I would (as a happy former owner) tell you to look closely at the Ranger 20.
Only caveat is that all
of the swing/drop keel boats at 20 to 30 years of age need to have their keel lifting or pivoting mechanisms inspected closely and likely some deferred maintenance will need to be done.
The heyday of these thousands of trailerable sailors was in the 70's and 80's and bunches of them remain, in back yards and the back row at marinas everywhere. A number of them were decent designs when young and can be brought back (like the Cal 21 or the Santana 21, to name only a couple) and some were awful-sailing boats even when new.
Like that villain in Harry Potter, we refrain from mentioning their long-out-of-production names here to avoid invoking wrath/loathing from the remaining owners, but if you ask back channel, the guilty can be identified...
BTW, while their production numbers were smaller, the Montgomery's were some of the classier trailerables, too!