Yeah, while I'm gonna hold out till EOL, at that time, I'll probably go to 10. I have it on my travel laptop, so can live with the GUI, but I really hate the way it updates.
By next year my current main laptop will be going on 6 years, so I'll be deciding if I'm going to do a 7/10 update or maybe getting a new laptop. I'd be happy to keep running 7 for years more, but lack of security updates is a no-go with me.
I'll keep at least one machine on it but off the Interwebz, because I have old work software I still dabble in that doesn't like 10. I actually do that right now with an old XP machine as well, for hooking up old hardware on a com port that won't run on one of those USB/COM dongles.
I dunno, I might try Linux as my main OS again at EOL. While I run it in VM, the last time I ran it as a main host, I was still finding some things too inconvenient and couldn't really get into Wine, though I probably didn't give it much of a chance. I just don't like dabbling in hardware/software stuff as much as I used to - I'm kinda becoming like an apple user in that regard.