It's weird. I had that exact experience with Linux. Had to reinstall the system from scratch every major distribution upgrades because they always screwed something up. Fedora's package manager corrupted its own database once. Support was just badly answered forum posts.

Then I switched to Arch Linux and never had problems ever again. Been running it for years with no problems despite its inexplicable reputation for instability. Whenever I want to do anything, I just look it up in the Arch Wiki which is the best Linux documentation ever made.

I have to use Windows at work and it's nothing but constant never ending pain. The god damn OS just does all sorts of stuff I couldn't care less about that have absolutely nothing to do with my job. It actually costs me money in lost productivity. All this for what? The only thing it does is launch the browser, and very rarely Libre Office when the network is down and I have to save a document locally. Yes, Libre Office.

On the flip side, I had the opposite experience. With Linux it was just the matter of compiling from the source. And most of the time, it would just compile without any issue. With windows, I needed to download MSVC and the whole studio and wasn't able to have the app running. I really did not understand why it had to be so complicated. At least with linux there is a support from the community because the same problem might have been encountered by someone else.

Further, in Windows, whenever I was trying new things or doing out of the normal stuff, it required modifying a lot of registry values. I found it horrible compared to Linux, where everything is a file and you can immediately change the file.

It's weird how people are still complaining about this stuff. I never have any trouble like this; I just use an Ubuntu-based distro, and get well-supported hardware (i.e., just buy a Dell or Lenovo laptop), and everything "just works".