Most of the searunners I've looked at have needed (or already had completed) some
repairs to the decks or around some of the many hatches. Fortunately on a
plywood boat the
repairs are very straightforward if not too extensive. These problems can be much, much worse on the polyester (vs epoxy) boats.
But remember on these type of repairs what you see from the surface often gets 10 times worse once you start to dig into it..
Overall needing winches and having been sailed for a few year with a blown
motor sounds like a bad case of deferred
maintenance (you know they didn't put $ into it if they didn't fix these things) that will show up elsewhere,...but it apparently still
sails & still could be a fair deal if the bones are solid!
For the right person, pretty simple to grease &
rebuild winches,
repair or replace (perhaps with used) the
diesel, or even throw on an
outboard and go...
Another thing to check for on a
boat like this would be waterlogged boards or mini
keel. The
centerboard if free of obstruction can be pulled up through the trunk while the boat is in the
water using the main
halyard.