I have a guests laptop running Mint, every upgrade means wiping everything off because there's no human way to do otherwise. My Windows laptop has seen upgrades in-place since Windows 7. And then while on Windows the updates happen in the background (from time to time asking for a reboot) on Mint I have to start them by hand, using one of the three update managers (still no idea what's what) and every time they throw also some errors, usually about outdated update sites/links but not only.