I have sold probably about 10 of my rides over the last 4 years and I only had a hard time letting go of one. I didn't need the cash but I couldn't justify keeping it as I had 6 bikes at the moment. It was a 90's aluminum Trek. Not a sought after bike but I loved it and it fit me like a glove. I actually posted it with a high price thinking it probably wouldn't sell but then I got a buyer and there it went. He actually brought it back a few months later for me to do some upgrades. The guy loved the bike and was enthusiastic about it so I felt good that I had sold it to him. I kept it for a few days and took it for a ride again. Although, I still have three bikes that I probably would never sell, hand down to someone - most likely. *edit: I'd probably keep them.