One thing I would key in on with the owner/broker is the boat's maintenance history. I'd want to know what had been serviced or replaced and when. I would not be shy about asking for repair receipts.
For example, I had all my standing rigging and chain plates replaced on my Hunter 30 in 2002. Should you just take my word on this, or should you verify my claim? Most owners would save these receipts. One of the reasons I decided to purchase my current boat was the fact the the engine had be recently overhauled and the owner showed me the repair receipts.