Strike 1 - The Marcon Cutlass 27
This is the first real sailboat I looked at with the idea I would buy it and live aboard. Oversized rigging, mahogany interior, full compliment of sails and a perfectly running gas engine. A fabulous opportunity at only $2000.
This and an investment opportunity in something called Microsoft in 1985 - too much thinking and not enough doing.
UPDATE 03/19/13: Go see her now @ http://www.damnboat.com/ . So glad to see it's not with some old geezer with no money..., wait that's me.