By the time I upgrade my computer, most of my software is ancient (by data standards) and I am ready for the new features.
My policy is that when I get a new machine, I update everything, run it until the next upgrade - or until I am forced to. I had a lot of my old software up until recently (when we did a clear out), but most of the stuff other than games was outdated and unusable because of real world changes. I don't play many games - I've got too many other things that keep me busy.
I do still have data files that go back to my DOS days. Much is saved to CDRs that are twenty or more years old but are still readable. I hope I live long enough to sort through all that stuff and dump the things that don't matter - old photos downloaded from CompuServe, for instance. From my Apple ][ (not +, not e, just ][) days I have been in the habit of keeping data separate from programs and the OS, so when I change computers it is easy to keep data and dump all the old software I don't need.
I think I tried an emulator about the same time I tried Linux. Problem was, it took up too much of my computer resources. I do photo and video editing. Windows and PhotoShop or the video programs I use were too greedy to run well in an emulator. They are why I have 32 GB of RAM and over 10 Tb storage, plus the fastest processor and video card I can afford. One problem with the current setup is that I have run out of connections for more hard drives. Externals get annoying, so I like to have my files where I can always access them and use external drives as backups.
The other reason I gave up Linux was that in 1999 I began a series of operations that lasted until spring of 2019. Fifteen major operations really screws up your brain and makes it hard to keep new information current, especially as I approach 70. That and five deaths in the family have cut into the time I have for non-essentials
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