The thing about missing paperwork is that there are 2 kinds. The kind you can get back, and the kind that you cannot. If the paperwork can be replaced to the point you can register the boat, then that's one thing. If the paperwork is irreplaceable (seems odd as a seller to not put the effort it to get it, if it's obtainable that's all) then it not a boat..it's a bunch of parts bolted together that can't boat.
I'm not sure what side of the operation you are on (Are you buying or selling?) If you are buying, and you are interested, throw him a low bone AFTER having done some legwork with the serial number and obtaining information on WHO the registered owner is, making sure he exists and is willing to sign and and get all set up to get the paperwork perfect. It may cost a few bucks, but the boat is not a boat without a registration, so without ensuring you can register you could potentially spend you money and not get a boat, but a bucket of parts. You can also give him deal contingent on being able to register the boat, show him what you learned about boat title in your research, and close the deal only with title in hand. No title no deal.
It's worth whatever you want to pay and the seller wants to take, before exchanging it. If nobody else has bought it yet, and it has been a long time in the market,it is probably not an awesome deal.
Good Luck. Ultimately the decision is yours. just be sure for your own benefit, you are not caught in a situation you can't get out from.