So I last made daily use of a Microsoft operating system on my desktop around about '00. It was that pig Win98, which drove me right into the arms of Linux, and I have never looked back since. (And no, Macs do not even tempt me. OSX might have some really shiny apps, but as an OS it is inferior to Linux, IMO.)
Fast forward to '13, and most or all of the damn banks in China insist on the use of Internet Explorer for their online banking. (Biting my tongue....) For various reasons, I am having to do this more and more, so thought it might be nice (and more secure) to be doing so on a legal, UP-TO-DATE, Win-something-or-other.
I managed to get a real cheap (legal, licensed, unopened packaging) copy of Win7 off of Taobao. Installed it in a virtual machine under Linux, typed in the serial number and had it accepted. And Windows Update did not work. Dies with some kind of (standard for Microsoft) completely useless and unintelligible error message. Probably has something to do with my accidentally clicking through the license code screen, and then adding the code after the fact.
And then I poured the rest of my afternoon down the drain, doing the Windows dance: tried a dozen different things, including an attempt to upgrade the same install from the same DVD image that failed (at the very end!) miserably. Finally I had to scrub the whole thing and start from scratch, being careful to give Microsoft it's little code at exactly the appointed time, and no other.
Ten years later, Windows still sucks.