I recored half the deck of a San Juan 21 and redid the transom, too, and I found out it is a low-fun project. It is much more involved than doing cosmetic work or fixing small areas of fiberglass. It's extremely messy and wearying work. It's not technically hard, but if it's not done correctly you'll get to rip it out and do it all over again.
-you have done recoring before
-you already have the tools (4" grinder, FeinMuliTool, scrapers, dremels, etc.)
-you don't mind working with these tools upside down right over your face
-getting clouds of fiberglass dust in every nook and cranny of your being
-you don't mind working with epoxy
resin for extended periods of time
-you have the time to set all this up and do it in a heated area (it's getting winter-ish)
-you are exactly sure how much of the deck needs to be redone and truly don't mind putting in the time if it's more than a few square feet
-you're absolutely sure that this boat is the perfect boat for you in all other ways
-make a low bid for this boat and realize that you are going to be spending a lot
of non-sailing time in it.
If you kind of want to be a boat fixer kinda guy then it might actually be fun, but if you're thinking it's a good way to get a deal on a larger boat I really think you'll wind up being quite frustrated. Personally I'd much rather spend a few more thousand bucks and get a boat that has solid decking and replace the rigging
or lifelines or sails or something.
Let us know what you decide to do.