Car tires = boat sails
That's a pretty good comparison, I think. Continuing it, would you pay more for a car with brand-new tires than one with bald ones?Sails have a service life, just as tires do. They get baggy (slows you down) and the stitching starts to come loose, and gradually lose their usefullness. This can happen in a few years - for a cruising boat using the sails every day - or 10 years or more. If the sails are new, and you're going to be mostly weekend sailing, they will last as long as you own the boat, most likely. What's that worth to you?Winches last a LONG time, 20 years or more of properly serviced. New winches are probably (hopefully) self-tailing, whereas the original ones on an older small boat probably weren't. Again, what's that worth to you?Personally, I think the telling phrase in your description of the boat is '...you can tell the owner has loved this boat.'That's worth a LOT, in my opinion. You can have some confidence that the engine oil has been changed regularly, the stuffing box hasn't been overtightented, the batteries have been serviced properly, etc. etc. etc.One other issue based on your location: If you are SURE the boat isn't a hurricane victim, that should count for something.I can't believe an owner - who presumably wants to sell the boat and doesn't have any other offers in hand - would be insulted or offended if you bring an offer of 10% less than asking price, of course contingent on survey with haulout and a sea trial.Good luck!Cheers,Bobs/v X SAIL R 8