First, in my opinion and experience, the difference in singlehanding
a 34 vs a 37.5 is negligible. More important for singlehanding is how the boat, lines, winches, etc are set up.
Regarding the boat, the Cat is a lot newer boat but at the end of the day, for any boat more than a few years old I would look at the condition, especially anything that would be big ticket to repair like engine
, wet core
in the deck
, old vs new sails