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Check with your preferred insurer....it's possible you might have difficulty securing insurance for a boat that is older than 20 years, or at least pay a higher premium.

I would also consider storage volume, especially for scuba gear (not sure how many sets you will have on board).

My vote goes to the newer model, although I think Catalina, in general, probably sails a bit better than Hunter. Even more, there are so many hulls available 27-30' range, 10-20 years old....I bet you can find a few other options the exceed both of the options you're considering.
 

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I'd like to understand what is your reasoning for the Catalina sailling better then the Hunter? I've never been out on a Hunter before (most of my sailing in the last 10 years has been on either little 14' lake boats, sunfish, a starcraft doublehull (NOT catamaran), or a 41' Columbia), and this one won't get splashed until the sea trial.
The C27 rates better on average than the Hunter, 200-215 vs 215-225. This is very much dependant on configuration (Inboard, Outboard, Tall Rig, Shoal Draft, etc).

Catalina built the C27 through the late 80's (1989?), although the original design was done in the 70's. You might find a newer model in better condition.
 
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