In 1984 I sold all of my bikes so I could move from Nebraska to Colorado (to be a climbing bum). I was worried I wouldn't have enough $$$ to start a new life. I really do regret selling my Woodrup Giro-tour, Gitane Super Course, Lotus ???, and Mongoose Koz Kruizer. I didn't get back into biking until 2007 (if I'd kept a bike or two, I might have not lost so many years!). I also sold my stereo system which will never be replaced...
Since 2007, I have managed to find another Woodrup
but regret selling off a Japanese Bianchi, a Rocky Mountain Classic, and a Trek 420 that would have been great for my wife (although the collage student I gave it to, really appreciated it!).
Cheers,
Chris