I still have an old laptop with XP on it; occasionally use it. Doesn't need to be updated because all the hardware works as well as it's going to, and I don't put it on the internet so not really worried about it being compromised. It does what I need it to, so no reason to get rid of it (and it couldn't handle an OS update anyway).
7 I like; it's pretty stable and you can dig pretty deep in customizing it. My studio machine is on 7; the only problems are caused by shitty drivers for my old audio interface, but I really don't want to sink the cash on a replacement that will give me the same latency/quality
8 however, is a mess. I have a laptop purchased last summer that came with 8. It's definitely designed for a consumer, rather than a creator, so the few things I've tried to do on it, I've usually given up and gone up to the studio machine. Fine for playing video games on or surfing the net. The actual Win 8 programs are a pain...EVERYTHING wants to run in full screen and without the taskbar, sometimes it's hard to tell what programs are actually running. I'm never doing just one thing (as a consequence, I'm playing less solitaire since the version that ships with it is full screen and useless to me). I haven't tried the classic theme yet, maybe that'll help. But I really don't want to try doing anything actually productive on it.
My Win8 highlight however was, while trying to kill a browser where flash had crashed (and locked up the machine...I don't blame that on Win8 though), the task manager locked up on me. In my decades of running windows (3.0 on my 286!) I've never had the task manager itself crash. Of course, I had the sense not to install WinME, so I could have run into it sooner. If the pattern holds, however, 9 should be 8 that actually works, so we'll see how things shape up then.
Back on topic, I have no problem with MS killing XP support. The fact that they've supported it so long is fantastic.