I quit Wndows 98SE for Linux and never looked back. I can upgrade my computers whenever I choose to, not when Microsoft and other commercial software producers decide it's time, or bog my machines down with "features" that are useless to me, or quit supporting features that are.
This is my usual upgrade path:
First, I keep full backups of my machines on at least two external hard drives and my personal networks.
Randomly I'll stumble upon a machine, usually someone else's e-waste, that is significantly better than my current desktop or laptop. I might add more memory or install a better hard drive.
I install Linux. In my case that's usually Debian, but Linux Mint might be friendlier.
Then I drag and drop everything from my freshly backed up home folder to the new machine.
There are a few applications I commonly use that are not included in default installs of Debian or Mint so I install those (for free!) from the repositories, usually when I realize they are missing. Most Linux applications are small and quick to install. There's no hoops to jump through to register them.
That's pretty much it.
I keep everything, and have files going back to the later 'seventies with emulators for most of the computers I once used daily. My favorite 8 bit Atari stuff is one click away on my desktop. So is my DOS stuff.
I've been doing this for so many years, on so many machines, that there may be pitfalls I'm unaware of. Problems with wifi adapters used to be common but that doesn't seem to be the case any more.
It just works for me, possibly because my computer use hasn't changed much since I first signed on to DU. I don't use proprietary photo or video editing software, I find that LibreOffice is more than adequate for my writing and spreadsheet needs, and I don't play modern graphics-intensive video games.
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