I belong to a group called Singles on Sailboats. There are 140 boats in the club, ranging from 24 to 50-something feet, of every conceivable configuration. Most of the boat owners are over 50 and average 60. Many join the club because they are "dock-bound". They can sail their boats thousands of miles single
handed, but they need crew to get away from and back to the slip. Smaller boats weigh less, and are more responsive. Equipment
is cheaper and the loads on halyards, sheets
, and dock
lines are easier to handle (with one hand, remember?)
There are two down-sides to smaller boats; The ride is rougher, and the bragging rights are diminished. This matters if you are susceptible to 'mast-envy'!
Properly equipped, with quality stuff, a mid thirties vessel will get-er-dun!