Age has always shaped our approach to boats and sailing in general. I just picked up a nice 1980 H27 as my starter boat (even though I have had cruisers the same size). My father recently moved from sail to power and I am happy to get him out sailing when he can. After all, he provided that to me when I was a kid.
My suggestion is trade in the 37 and get a 27 or 30. You know what to expect with our vintage Hunter and the maintenance costs and time required are significantly lower. From sanding to yard fees you will not be bound as tightly financially and time wise as with a 37 footer. In fact, they make trailers which can easily haul a 27 or 30' keel boat with a heavy duty truck. This means you don't have to go through the process of chartering a big rig to move your boat. Also it expands your search area when looking at boats for sale.
My suggestion is to spend a good bit of time finding a good deal. You probably have more time than money for now and taking a good look at the used market is a good idea. In my area I know there are at least 5 H27's from the 70's - 80's on Craigslist.
I guess I would give the same advice I read in a book titled, "Sensible Cruising: The Thoreau Approach : A Philosophic and Practical Approach to Cruising". It's on Amazon. Basically the author states, get the boat and get out on the water. Don't get bogged down with maintenance and big boats.
The 27 should give you a good feel on a smaller lake. Kinda big boat when you are out there, but the boat is still manageable on shore, at the dock or on the road.
Good luck and let us know what you decide to do.
