Before I quit on this boat, I would do some research on Huckins. One of the most respected, and highest quality builders for many years. I would assume that the "fiberglass over wood" you mention is as the boat was built, not a later fiberglass do-over by someone other than Huckins. By 1969, Huckins was at the forefront of what is now the "cold molded" fiberglass over wood method. Their boats were FG over mahogany, with a fully resined interior. Very strong, generally very light for size. Also very high quality work. The same family has owned and run Huckins from the beginning. If you know the hull #, I am sure they will be happy to tell you pretty much all you would want to know about that particular boat. From a quick search, $100K for a 65' 1969 Caribbean is actually a pretty low price. If that is the type boat you are interested in, IMO it would certainly bear looking into.
If it is the one on Yachtworld in Grat Bridge, VA, I would definitely take a hard look at it. From the pics, it is quite a good looking boat.