Pull the boat, Jim.
Cracks in the Gel-coat, seals around the shaft, etc. can only be spotted out of the water.
Here in Maryland, it is $20 bucks or so a foot to yank a boat and put it on blocks, which I recommend highly.
Baseline the thing BEFORE you buy it.
From the pictures, there is a whole lot of work that needs to be done to get the wood right, above the waterline up to speed, etc. Hire a pro to tell yo what needs to be done.
What you'll save in engine, fuel tank (old gas and I bet the blond owner never heard of Stabil
), old piping and tubing repair, etc. is worth the price of admission.