I run both Linux and Windows. Laptop is only Linux and has had multiple versions, Fedora, Debian and now Arch. PCs are always Windows with Linux available in some form.

Windows has definately improved for me over the years. Sure you get a few app compatibility issues (Bioshock 1+2 are one that come to mind) but the actual OS has become pretty rock solid for me. I feel it still gets some unfair treatment. The privacy issues can be solved via 3rd party tools or manually if you're comfortable doing that.

1st PC: Windows 98 (1st edition), not greatest. Windows crashed on 1st ever boot/setup out of the box and had to run a full scandisk check. Had a hardware/driver issue appear after several years. Wouldn't say it was a driver issue as nothing really changed in updates. Also had Mandrake 9.2 installed, after bricking a previously unknown brand cd drive during installation. Found a small label afterwards, Goldstar = LG, which interpreted flush cache as update firmware. Could never work out hardware issue because every option ended with why does Linux work.

2nd PC (using good bits of 1st): 98 1st again with install transfered from old machine. Nothing but the odd blue screen. Upgraded to XP 1a adding another 256MB RAM. Only issue was installing Office 97 (for other family members, I had OO.org) which had to be done prior to SP3 install. Occasional blue screen. Linux running via CoLinux.

3rd (1st self built): Vista. Hand on heart don't remember having 1 blue screen from 2007/8 up to summer 2014. Gets a lot of criticism but I never had an issue with it. In some ways more secure than 7 as they relaxed permissions (less pop up are you sure messages) on some componenets. Virtualbox used from now on.

4th (current): 7 Home Premium, won't touch 8 with a barge pole. Can't say, never actually installed as I ordered wrong version by mistake (too much RAM). Sent back and replaced with Pro. No issues what so ever, no blue screens.
Upgraded to 10 Pro end of July. One issue with settings manager cured by a reboot. Can't say about Anniversary update as it hasn't appeared in update yet but not too fussed as they have to sort issue with game controller.