Multiple Catalina 27 owners have gone this route that I have spoken to in original search. I went from a 23 trailerable with outboard (1 ton/w 900 pd swing keel) to a Catalina 30 in 2005.
Looked back only to contantly realize I shoudl have done it sooner. Get the 25 if you can.....although mine had a 5411 Universal and now has an M-18 (about 15 horsies) Have a Tall
rig and Bowsprit.
Put almost 400 miles on her this season around Long Island Sound in up to 5 foot seas.
Roomer then 10M Pearsons, Beneteau Firsts, Pearson 303, etc. at 180-ish PHRF handicap she is a noble comeptitor and even if you loose you can have the party in YOUR boat......hell of a cruiser! I have a current friend (as well 2 of the previosu owners of my boat) who have gone to a 34 Catalina but almost all comment they did not get that much more boat just some nicer equipment and details. So staying in the brand is VERY common.