My laptop at work upgraded to 10, went smoothly, didn't lose anything. The update nagging is certainly annoying, though I just set it to automatically do it at like 6pm, so after I've left. The more I've heard about 10's behind the scenes privacy issues, the less I like it. I found the fact that it will appear to let you turn off the auto updates and the nag screens, but literally once you're not looking, will turn them back on again.
My personal laptop I've struggled with windows from day 1. Finally got sick of it, wiped the hard disk, and installed Linux Mint last time.
Mint is the most "windows-like" of the various flavors of Linux and probably the easiest for a Windows ex-pat to get used to. You get a desktop, "start menu", icons, ect as you'd expect, nothing too weird. There's a bit of a learning curve, but once I got used to it I greatly prefer it. My aging laptop is significantly faster than it ever was on win 7 or 10 and have had zero issues with hangs or crashes. All the software I realistically need was built in as well- full Office suite of programs, browser, email, iTunes clone, media players, disc burner, ect, and all of it is free and full versions. No trial versions, no ad ware, no BS. It's all there, it's all free, it all works. Wish I had done it years ago.