I use FreeFileSync to synchronize my Thunderbird and Firefox Profiles, KeepassXC files, web server stuff etc. I also prefer portable applications that keep their preferences in their own folders. So I also don't mind if a machine randomly dies, but I still have all my stuff locally, plus backups, and what I upload is always a copy. Other than stuff that lives on chat servers or social media, of course, Soundcloud and YouTube playlists -- but that stuff, but that stuff will go away sooner than the files I have locally. Stuff that lives elsewhere is just a way to interact with others and show them things, not the keeper of anything that matters to me.

The downside is that I can't just change machines nilly-willy, I need to sync first, at least if things overlap. For example, I can use one Firefox profile on one machine, another on a second machine, and use Thunderbird on a third, but I can't use the same profile on several machines without getting a merge conflict, so to speak. That was confusing and annoying for like a week, since then it's not been a problem, and by now I'm so pampered by it, I simply avoid stuff that doesn't play nicely with my workflow. Smartphone apps, for example, or programs that doesn't allow me to configure the paths it uses, and so on.

Since I use applications and work on data, the OS doesn't that matter much. I mind changing Windows from the ass-backwards defaults much less than sticking with the defaults, and I do that as I go along, i.e. when I use a feature or get annoyed by the default, I just change it. That doesn't require any thought and very little time, so the configuration I would have to repeat on a new system isn't something I consider valuable, I'm pretty sure it takes much less time in total than working with the default config, in the long run. If I had to do it more often than every once in a blue moon, I'd find ways to automate it.

I am just not interested in something that could go away based on the decision of some pointy-haired boss, which is tends to be inferior software in the first place, anyway. Like, compare Directory Opus with Windows Explorer, one is a serious application, the other is a toy that constantly gets in your way.