Cata lina 25
Comparing Catalina 25s I have a fin keel standard rig. My close friend has a 25 wing keel tall rig. My draft 4 feet, his draft 2' 11". He has a trailer, I don't.
Both boats can sail side by side for hours.
In very light air his is faster.
Downwind in most conditions his is faster.
Upwind, especially in strong winds, I'm faster and point higher (by quite a bit).
If I fly a 155 jib and he a 135 we are essentially the same in moderate air, non racing conditions.
I'd reconsider the inboard diesel. A Cat 27 with an outboard would be fine on a lake. Much cheaper to own and operate.
Comparing Catalina 25 to Catalina 27 we both sail about the same. I've raced extensively PHRF against a 27 and he usually wins, but I have some wins.