The last few months Windows 10 has been pretty stable. But for the previous two years, updates were constantly breaking things.
One update changed drawing tablet behavior, so I could no longer reposition windows using the pen. For some stupid reason (favorable reaction among a test group of filthy tablet PC casuals) Microsoft decided that pressing and dragging with a pen should now scroll the contents of the window, making it practically impossible for me to work with Photoshop. I had to find a registry hack to undo their change.
Several updates in a row broke the Unreal Editor and the editor crashed every time I tried saving something. My workflow was 100% destroyed by those updates. I lost about a week of work rolling back updates, which Windows would then automatically reinstall. You can't opt out of updates unless you have a Windows enterprise license, where the sysadmin sets the schedule for updates. All non-enterprise users MUST install updates as soon as they're available. Your only other option is to never connect to the internet. I had to work around that by telling Windows my connection was metered, and then setting telling Windows Update to not download updates on a metered connection.
Another update broke DX9. The old DX9 knew that decals get written to the depth of the object they're displayed on. Updated DX9 had no idea what depth the decals were at and my game's visuals were completely screwed up.
Cortana uses up an unacceptable amount of system resources. And I can't stand the cutesy personality they gave it. One of the first things I did after upgrading to Windows 10 was turning off Cortana. And then an update turned it back on and wouldn't let me turn it off. And they took away Windows search. The search bar is a Cortana search that also grabs Bing results from the Internet. I don't want Bing results. If I want Bing results, I'll open a browser and ask Bing. When I use my search bar I'm looking for my own damn files on my own damn computer. It took another registry hack to lobotomize Cortana again and get back a regular search bar.
Edit: While I'm complaining about Windows, let me add this even though it wasn't specific to any one update. As soon as I plugged in a drawing tablet, my desktop PC decided that it was a tablet PC. A handwriting window hovered over everything. All of my drop-down menus started appearing on the wrong side. I had to go specifically find all the tablet PC options and turn them off. There was no option for "turn off putting the drop-down menu to the left of the menu button." I could only tell Windows that I'm left-handed, so it would put the drop-down menu back on the right side of the menu button where it belongs.
I've also disabled notifications for everything I can find an option for. (Not being able to disable Norton's advertisements and "we're keeping your computer clean" notifications was one factor in why I canceled my subscription. That's the kind of behavior I expect from freeware. If I'm paying $100/year for a program, I want it to shut up and stay out of my way.)
What I wish is that default Windows behavior was "don't do anything unless specifically told by the user," instead of current default behavior, which is "turn on every possible annoyance and make it really hard for the user to turn any of it off."