I personally don't understand what "maintaining linux" is. I have a dock icon that says "update available", and then I click "update", and it runs the updates. Never had any problems with that (Linux Mint).
On Windows, each application has their own update schemes, and it can all go wrong there. And the updates of Windows, what a pain! All the "don't shut down your system now" kind of things... horrible.
This is not the olden days of Linux anymore you know, it's just all super user friendly. I would say more user friendly than Windows.
Try to do a major Windows upgrade, and compare that to a major version update of Linux.