Linux system upgrade may not be much better
As someone who's been happily running Linux on the laptops and desktops in my life for years.
The actual ability to run a dist-upgrade successful may not be a lot better. Put cd in, install it'll almost certainly just work. Several years later when you want to update to the new current version? Consider starting from scratch with the new install cd
I'd be surprised if windows 10 didn't work on your machines, in place upgrades are hard though...