Thats actually a funny coincidence. Windows 95 was kinda hilarious.

So, there lies the problem then: being and admin/poweruser is very different from being a user. You make things work in different ways, make things work for others (helpdesk) who may not be as formidable in using windows.

But what I don’t understand is: if you write software, you often have to install tons of stuff which then make problems for example due to the windows firewall not updating. I thought a dev would experience that as well.

Any my personal favorites: trying to upgrade windows versions, the fucking rescue partitions on oem computers where you dont get a license key which you can use to do a fresh install but have to restore the infinitely bloated oem version.

If you work on cutting edge hardware or at least very freshly realeased hardware, the constant driver issues, having to use things like this driver tool that I forgot the name of to actually have the best drivers for your hardware and so on.

Then there was the buggy messes called me, vista and 8 which were a constant struggle against badly written code and idiotic, hard to deactivate features.

TL;DR: Windows works if you don‘t ask to be private, performant or secure.