I end up with seller's remorse nearly every time. I tend to get attached to things, which I know is completely irrational, yet it still happens. If I could, I would keep them all. But my reality right now is if I want something new, something usually has to go to help pay for it. I usually find some little flaw or quirk in the game to focus on and justify selling, only to regret it after a few months. I have bought games back a few times...in some cases even the exact same machine. It's a vicious cycle with me. Right now I am thinking of getting rid of one I already bought, sold, and bought back...and my likely replacement would also be a repeat. And the sad part is, I'm pretty sure at some point down the line I will miss this one again and be looking for another one. Terrible I tell you...terrible. LOL
I will say though, that is one of the beautiful things about this hobby. If you buy one you don't enjoy, or just need a change, you can sell pretty easily. If you regret a sale, you can always find another one. If you are smart about your buying and selling, you won't even lose much if any money doing so. So really, why not keep it fresh when the urge hits. For me the biggest regrets are probably the ones that I bought NIB that I know I will not be able to (reasonably) replace with another NIB. There is something a bit more special about the ones that were "all mine". But that is probably just another silly personal mindset.