... I still have a few Windows 95 and 97s lurking about. My "main" machines are windows XP, version 7, and version 8. For the Windows 8, I purchased an overlay for it that makes it look exactly like Windows 7. Fortunately by pure luck I missed the entire "Vista" iteration. The next machine will have whatever Windows is the current at the time and it will stay that way until I retire it.
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Iron Horsemen you are a wise man, Upgrades are and always have been a messy proposition. They can leave behind many issues and incompatibility with so many various manufactures of PC parts and software makes upgrades a tricky business at best.
I have a friend who has abandoned the PC all together for his gaming because of compatibility issues. He now plays exclusively on consoles. Download the game and play!
Almost every upgrade I do, I always do a complete reformatting of the hard drive and do a clean install. I even let the OS handle the formatting because it eliminates the possibility of compatibility with file systems.
What about Windows Millennium Edition? That was not around long. I had a ME PC and it worked fine, but not many fans of that OS either.
Trying to use outdated equipment for new operating systems can be a nightmare. Microsoft has done a great job for the most part, but now even high end PCs are very seldom 100% IBM compatible if there even is such a thing. Worst yet are low cost out of date systems. Trying to make complete backward compatibility for all systems is just not possible. Add to that the software developers unwillingness to invest in upgrades for their products. Like the old saying "you can't please everyone"
How about E machines? Forget upgrading those disposable things.
I wonder how these new Chrome machines are?
My children and I have had good luck with Windows 10 upgrades, thank God.
My current PC was a hand-me-down from my Son-in-Law he has to have the latest and greatest. That's good for me, because I like free! No wonder I think so highly of Windows 10, hard to beat free.