About 4 years back now, my wife and I we're just recently married, and she lost her job due to the economy. There was about a year-long gap between that job and her next one, and at the time, I didn't have a good enough job to cover our standard of living. Because I was young & foolish, I didn't adjust our expenses accordingly, and instead sold-off things & racked-up debt to pay for activities.
Regretfully, I sold my Sega Genesis with 30+ games that I had since I was 8, a used Super Nintendo I bought in really nice condition with 10 games during high school, and a Gamecube I bought right before college, and played endless hours of Megaman & Smash Bros on.
I technically have the money on-hand to repurchase these things, but I don't have any guarantee that they'll be in as good a condition as the ones I had. That, and at this stage in my life (demanding career, wife, a 2 year old, and another one on the way), I just don't think I would have the time to play it all if I recouped them. Maybe someday 4-5 years down the road when both my children are old enough to play & appreciate such things.