Hinckley is one of the few boats that have enough of a cult following that their older models sell for an amount that would be crazy if they were any other brand/builder in the same condition. Good boats certainly but any 30 or 40 year old boat has issues and Hinckley is no exception. In today's depressed market there are great values out there but 99% need work. To pay several times as much for an older Hinckley than for a comparable boat without the cache of the name doesn't make sense really.
The Contessa 32 probably sells for a larger amount than it really should, mostly because of Fastnet 79. Good boat but certainly not roomy and wet as well.
Based on prices asked and selling prices for the Vega 27 I don't think the voyages made have really added that much to its marketability.
The Alberg 37, if in good condition, compares well with many boats in the same size range that sell for much more and could be a very good buy.
One of the gems from the past that many ignore is the Chris Craft Commanche, designed by S&S - very similar to a Swan from the same era and for only a fraction of the price. Swans are another boat that sells for more than the physical boat is really worth, buoyed by the name.
Commanche on YachtWorld 1970 Chris Craft Comanche Sail Boat For Sale - www.yachtworld.com
I am very familiar with this design. Same as the boat Glenn Wakefield is sailing around the world non-stop currently and awesome to weather. At almost halfway around he has averaged close to 120 miles per day to windward, solo.