Yes and no. Depends on how much pride they seemed to have in their collection before they decided to shed it off. If they're the type who jumped in and bought 1000 games in one year's time, then decided to get out of it, that doesn't bother me. But if they spent years picking up games on the cheap, slowing building their collection and you can tell they take a lot of pride in it, then something comes along and they axe a bunch of it. That kinda hurts to see, even if it doesn't bother them to do it.
For me this is a one trip journey, and I'm never going back. If something ever happened, I'd just emulate games when I felt like playing, and find another physical hobby to pursue. The prices, scarcity, and popularity of this stuff nauseates me to even think of doing-over. Plus so much of it was about the discovery, and the game hunts and special finds that cannot be recreated.
It doesn't pain me to buy from a collector. I'd much rather see their games go to someone else who is ecstatic about them than into the hands of a re-seller or something like that. What gets me more, is buying or taking games from someone who was
not a collector, but just had a few old games lying around from their childhood. Here I am with a million games, and I'm taking their childhood stuff away most likely to throw on a pile.
That doesn't sit well with me.
I've considered downsizing because I have a number of things that I bought for the wrong reasons, but don't know if I could actually do it. Still have a stack of FMV games for the Sega CD I've disowned, but never gotten rid of.
Have about 100 games that I have no desire to ever even try, would like to shed those, but probably won't. Maybe one day, after I've tried everything I own, I'd feel better about getting rid of some.