[sailingfool]

....
On the hand I've got the newer Hunter that shows very little evidence of having ever being used, aside from a bad paint job on the hull that's peeling in spots, and needs scraped (sanded?) and re-painted. ...

In my opinion that these two boats are comparable in price reflects the fact that the Cat 27 is much better built boat than the Hunter, and just well, more desirable, and always will be. You are buying a sailboat to sail, buy the best you can, it ain't an RV.

I can't see how you can so easily discount the crappy paint job, I assume you mean on the topsides, not a bottom job. If it is the topsides, you cannot easilky fix a poor paint job, you need to totally remove it first. To improve the appearance, you would need to take on a very hard and long job to remove all paint to down to bare gelcoat and properly paint it yourself, which at best can promise mixed results. Or pay probably the purchase price all over to have the hull professionally painted, the only way it will ever look good.