Well perhaps I'm a more trusting sole?
It sounds like this may be an expensive boat, so all these comments are relative. Also in all the sailboat purchases I have had it is always the systems that are the weakest link. Having said that,
First, I would find the best, most detailed surveyor in the area, preferably one that has done several of your make and model. I had one surveyor years ago tell me that brokers didn't like him because he always found things wrong and was very picky...my kind of guy. You definitely need to be there with the surveyor. Talk with him ahead of time and let him know this, ask questions and learn everything you can. All boats have wear and tear, I of course want to know the major issues but I want to know now any minor issues or potential issues as well. Of course on the hard the surveyor can only do so much. But his survey and my personal observations will tell me know how to proceed. If the surveyor says it is one of the best examples he has seen, that would give me confidence that the boat had been well maintained. I might proceed to buy the boat, hold and acceptable amount back in escrow for any unforseen issues that crop up once the boat is in the water. Have the seller also guarantee that all systems were in working condition last fall and he will agree to repair anything not fully operational. Alternatively, if the boat is in average condition with a lot of little deferred maintenance type things I might try and work out a long escrow with the seller. Or make sure I hold back plenty of money in escrow. I also would try and talk directly with the seller to gauge his character. If I was the seller and you talked to me, I would tell you everything works fine, I expect you as the buyer to have a boat that everything works on, and if it doesn't I, as the seller, expect to make it right. Now, I as seller, am not going to give you a brand new equipment if something is wrong, but I will authorize the yard to repair or replace as necessary. On the other hand if the seller isn't willing to be co-operative and is vague with his answers, then keep looking and wait until spring and see if it is still available. Put yourself in the sellers shoes. I think an honest seller would have no problem agreeing to fixing things and holding back some money for that potential situation. But an honest seller would much rather have a sale with a hold back than no sale at all. I as a seller wouldn't want a long escrow as I'm looking for a sale, not to take my boat off the market. Get the survey and go from there