South shore of LI, presumably in the Great South Bay? And you're paying $1600 to have it trucked up to CT?
That's the only part I'd call madness. If the boat works, if the engine and sails work, it will be an easy 3 days to bring the boat home. First day, either up the East River and into the sound, or around the east end and into the sound. Second day crossing the sound and probably hitting the river, third short day home. All you need is the weather window and there's some fine saiing in November, you just need to consider a watch cap, warm footwear, warm underwear, and gloves. Thin neoprene gloves in case there's a cold rain, but hopefully you don't need to go into that.
Of course, that all presumes someone has made sure the boat is safe and reliable--and I'd rather invest that up front in a survey and engine mechanic in any case, because that needs to be known no matter where the boat is or will be going. If the PO is willing to help you sail it home--that's probably a sign that he has some faith in the condition of the boat.
With all due respect to Mike, sails from 1979 are either shot or haven't been used. Even the best of canvas stretches out of shape, chafes, degrades from UV exposure. I had a friend with an old Chrysler wagon that ran just fine without any maintenance. Then we changed the spark plus and found that two of the original six actually had been consumed by the engine. With six all new plugs, it ran one hell of a lot better. Everything is relative.
31 year old sails? "Homey don't think so." Not if you've been SAILING with them.