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I guess that I would have to ask, how do you plan to use the boat and where you sail. Hinckley Pilots have always had a warm spot in my heart. These were the first boats that I ever crewed on in a race. They were well constructed and beautifully detailed. There is a different aesthetic to sailing these old boats that can be very appealing. Boats like the Pilot make good daysailors and weekenders in a sailing venue that has predominantly moderate winds and rarely experiences short chop.
By any objective standard, these are very expensive boats for what they offer. For the money there are a lot of newer boats are easier to handle, offer more comfortable accommodations, and better performance. Comparatively speaking, these boats are miserably wet and tender in heavy going and require a lot of skill to sail in gustier conditions.
I have seen examples of these boats all across the price range. A few years back I looked at an unrestored 1960's model with its original Grey Marine gas engine with an asking price in the mid-$30K range. I have seen a restored version with a carbon fiber mast with asking prices in the $150K range.
I actually exchanged e-mail with a fellow who had a restored Pilot with a carbon fiber mast, an altered sailplan, and modern sails. He indicated that the carbon fiber mast and new sail plan really transformed the sailing characteristics of the boat. In his case the carbon fiber mast was taller than the original aluminum spar allowing him to carry smaller overlapping headsails, which made the boat easier to sail. He reported that the dramatic weight savings aloft allowed him to carry sail longer, and reduced the feeling of the boat being overly tender. He also replaced all of the deck hardware with more modern gear which he reported as really making a huge difference in ease of handling as well.
Jeff
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