Gaming

You own a version of the games, sure, but the version you own is effectively useless on a modern system.

Perhaps the taste is less sour if you consider what you are paying for here is someone else doing the hard work to get an old game to run on modern hardware, saving you all that frustration and effort and time.

Well not if you can dig up and get running the computer you bought the games for, or one say 5-10 years younger. Windows XP will do for anything on a CD, Windows 95 for anything on a 3.5 floppy. 5.25 floppy then most will run on 3.1.

It's just that it's a lot of work ensuring backwards compatibility and it's not always a good idea, I'd argue the software world, in general, strive to much for backwards compatibility but that's another discussion.

That work needs funding so it's either pay GOG for the work that has been done remaking parts or repacking to make it run on modern computers. Or look to the hobbyist side of things but since they aren't paid, they of course seldom package what they do in an easy to consume format leading to enormous guides with 20 steps that maybe works, but probably not if you don't have an exact setup like the guy who wrote its.

Unfortunately in the 2020s you don't even own the games you have the physical media for.

Edit: as a more serious answer, Linux might be a better bet than Windows for playing windows games (ironically), either through Proton or Wine.

Gog has some ways to claim drm-free digital versions of gsmes you bouhht elsewhere. May be worth a shot.

From GoG specifically, as they patch the older games on their store to "just run" on modern Windows