It's never about spending money.. if you have the disposable income and enjoy collecting something then no issues. And I'm not giving up collecting retro hardware or software. However like many others in the retro scene I always collect stuff that I wished for at the time and can now suddenly own and smile that I finally have.. but times have moved on and other than as a curiosity to tinker with a lot of it really isn't that useful for productivity any more.. and there is a lot of retro hardware I no longer have a need for and will never use again.

And now we have Everdrive's for consoles, and USB floppy drive emulators for computers (Gotek and HxC) we really don't need to horde quite so many original games for them either.

Regarding PC games, as you mentioned, I've actually been grabbing older games I owned on physical media when they come up on sale on Steam. That way I will always own a copy of the games I enjoyed in the past, with an easy way to access and reinstall them if I ever want to play them again. I can then get rid of the original boxed versions and free some more space. It is the software more than anything else taking up the space.