What would you buy for $100,000?
I would have to say, in my completely unbiased opinion, that you should buy the C&C 37 CB I''m trying to sell <g>. She''s got a centerboard, great for those Chesapeake shallows. At $68K you can still buy some of that Bank of New York stock afterwords.
She''s actually a solid, great sailing boat. There''s a lot of those out there - boats of a certain vintage like C&C, Sabre, some J''s, etc. that you can get for under 100K and have a great sailing experience.