I think the most damaging think for me, was that MS backed me and the people I support into a corner over 10 - and not *just* for the 10-y reasons we're all familiar with (of course them still being a factor).
Have you tried going with an older Windows version because you don't want 10 and trying to update it? It's a sysphean struggle that would make a saint look someone from Geordie Shore.
I tried to set up a Vista machine this week (don't ask, yeah yeah). After a bored-to-tears 2 hour wait, it was *still* 'checking for updates'. Putting down my noose, I decided on a an experiment. The user only wanted something to launch Citrix from...
I grabbed a Mint ISO, made a boot stick, and in under 20 minutes I had a laptop that was re-animated with rude life, had official Citrix installed and working like a champ. A whopping 10 minutes later it was fully updated with just 228MB or whatever of patches.
Windows 7 is the same now, if you try and update it and then when you eventually fight your way through the minion patches, you lose all your lives on a GWX experience at the end. I just can't bothered.
To this this end, MS have done the worst they can, by just slowly atrophying my interest level in maintaining Windows.