Started on Win 3.0, then later upgraded to Win 3.1. I have fond memories from back then, but I don't miss them much now. Neat to load and say "ah yeah, I remember this." But not much else.
Win 95 changed my world view though. I guess I was at the right impressionable age, because the release excitement felt huge. I got hold of a beta via a BBS (apparently they weren't authorized to distribute it -- who knew??) and was SO impressed by how ... different it felt to DOS / Win 3.x. I still love Win 95.
I tried 98 FE once, and it failed so hard that I pretty much skipped 98 entirely.
Win ME worked really well on my PC back in the day, and so I used it for a few years. Quite enjoyed it, but then fell in love with BeOS and reverted to Windows only when necessary (games, SB Live stuff, other special software).
I tried Win 2K but didn't have enough horsepower for it. Sluggish. Poor driver support for consumer hardware, at first. Went back to ME.
When XP came out, I had the "Fisher Price" reaction as well. Oh look, computers are made for dumb people now. .... but I did kind of like the clean, white menus. And the plastic didn't really look so bad. Nice wallpapers. Boots fast! It's really stable. And, before I knew it, I was an XP fan.
Vista got the same bum rap as 2K. Installed on a P4 with not enough memory to really get a fair shake. Decided to skip it.
Win 7 was surprisingly lean, having been gutted of all the cruft in the source code over the past few years. I gradually became a Linux guy, then a Mac OS guy, but still like Win 7. I have a couple Win 7 PCs at home, and a VM on my Mac.
Tried Win 8 once. Sucked.
I tried Win 10 both as a VM and standalone. It did NOT seem fully baked yet, and I hated the dichotomy of "old Windows" and "new Windows meant for a touchscreen you don't have", where the dividing line seemed to be arbitrary -- like they just never got around to revamping the dialog boxes. It felt like a new coat of paint on an old junk drawer. Plus, I can't get over the dialog text. All the words are small so you can understand what they mean, but the underlying message is really obfusc... I mean, not very clear, so you can't again.