Regarding Linux machines, I frequently hear "oh yeah I haven't had to re-install Linux in 5+N years, my computer just keeps running fine!" Linux system maintenence, bug-squashing, documentation, and fix-applying is all very transparent.

Over in Windows-land, you frequently hear "oh yeah you gotta reinstall Windows every couple of years, or whenever you do xyz operation (say, disk cloning)". Troubleshooting Windows is a huge pain in the ass. There's no good centralized documentation, SEO sucks, registry hacks are common, etc. I've spent much more of my computing life on Windows machines, and I still have no idea how they truly work. I have no idea why sometimes the only way to fix an hardware/driver issue is by running the built-in troubleshooters, etc.

My last job gave me a windows machine. I tried using Windows Hello for login and... it broke Outlook. Apparently this was a known bug.

My solution? Type my strong password at every reboot and move to using the Yubi key they offered me. Great, I like Yubi keys. Oh, I can't set a security key as my primary means of 2 factor? My options were Hello or using the Microsoft authenticator phone app (couldn't use my other OTP app...). So every single login always started with "Sign in with Hello or use a security key". If using Hello I could just tap my finger and move on (and Outlook might crash silently). If security key I had to go through this dumb process of clicking: "use another device", "security key", "next", "type credentials", "tap security key", "ok". I think that needless "next" button was what really got under my skin. It was already a manufactured problem but an extra dialogue screen that is just doing nothing. Quite Kafkaesque.

The flip side though is that on Windows you can run an installer from 20 years ago, or sometimes even just copy the program directory over, and it will work. You might not have to reinstall Linux, but you'll have to update it and sometimes those updates mean that old stuff starts working. The big win of Windows for a long time was that old stuff would still work no matter what, and you could maintain old workflows on newer computers till kingdom come.

That advantage has been lost with Win10, which jumped on the constant-update bandwagon and took control away from the user. For me that's what tipped the scales to Linux.