Re: Buying a Cruiser
I think the biggest problem is that your current use the Chesie, is not really conductive to full keel boats as there is the preponderance of light winds. Your description of use is really coastal with a few longer hops, so why put up with the performance hit of a full keel cruising boat in 99.9% of the time in case in the future you might want to go through the canal and across the Pacific? Why not get something that suits you needs now and in the foreseeable future, does not have to be your for ever boat. Just choose something that will sell reasonably quickly (fairly popular model) and you will not likely loose money as these older boats are all pretty much depreciated as much as they can.
Then if 10 years down the line you want a heavy cruiser you can trade to it. I can't see buying something in case you might want to do it 10 years down the line. In the meantime you can create a list of what you really want.
Certainly what you describe doing has been done by thousands of Hunter/Catalina/Beneteau/Cal/Ericson/et all in the past. You are not talking long off shore passages but island hopping for the most part. Heck we have Arron here on the site that does regular hops from Florida to Central America in a sub 30 foot Columbia (if memory serves me right) with no motor.