Well, my main problem is that with Windows 10, there are many old driver you cannot use anymore.
I've got a Wacom Tablet with serial connector. Yes, it's old, but it still works fine. The last officially released driver was for Windows XP.
It didn't even work anymore with Windows Vista or 7, but by manually hacking around the driver, you could at least get it to work.
With Win 10, it's impossible it seems.
With Linux, it works out of the box. Install the Wacom drivers, connect it, and that's it.
Once a driver is included in Linux, it doesn't get lost or stop working in future Linux versions.
With Windows, it does. And that's not the only driver I had issues with.
Flashing a GP2x also is impossible with anything more recent than Windows XP.
That's my main problem. I know new Windows Versions are made for more recent hardware, but some older hardware could still be used on current Windows if they kept a compatibility stack for the drivers.
For me, this is seriously broken... and a big hassle to work with.
Another issue I have:
I just upgraded my PC. The only thing I kept was the harddisk.
With Linux, all I had to do was put the harddisk into the new system and boot. Everything worked out of the box. Perfect
With Windows...? You'd be lucky if it even boots. And then you'd need to reactivate it, search for all drivers, etc.
And finally:
If an installation totally crashes (and I mean totally, so not really fixable).
On Linux, I save the home and etc-directory as well as the installed packages as a list using a live disk, reinstall it, let it automatically reinstall the packages from the list, copy back the home directory and important configs from etc, and that's it.
System works again, with all users, programs, etc.
Usually takes 30 minutes - 1 hour.
On Windows...?
There's not even an easy way to boot with a live disk and save the config of the users.
And copying them back after an installation (where you also need to reinstall all programs manually!) is even more problematic, because of the weird permission system it has.
Usually, I expect about 3 - 4 hours until the system is reinstalled and MOST things should be configured again...
All that WAS better back with Windows XP.
So yeah, for me, Windows has become worse over time.
And it doesn't help that the UI is a mess.
Just the settings of Windows 10 are a mixture of old and new settings dialogues.
Depending on what settings you want to change, you get a totally different layout and style... they should've ported all old settings to the new UI as well.
For Printers, you even have TWO settings dialogues: The old and the new one.
The new one doesn't even seem to work properly (it often fails when installing a printer, while the old one works).
10 years ago, Windows users were making fun that with Linux, everything is a mess and the UI looks unfinished, as some programe ran with GTK and some using QT, and they all looked different.
Now this has switched around. Having GTK apps use the QT theme is no big deal whereas with Windows 10, old and new layouts and styles are even mixed in Microsofts very own settings management...
Oh boy...