@shansterable @PurpleJillybeans You can get a long way on your own, the cliff for Linux is not so much daily maintenance it's having the confidence that if something goes really wrong you can fix it.
If you're able to find somepony that you know who also runs Linux and that you're not scared to ask questions of or to let look at your setup, you might not need to ask them very much very often, but when you do need them, it can turn a 3 day pawblem into a 1 hour pawblem.
@shansterable @PurpleJillybeans Honestly, for me Linux is mostly set-it and forget it. :3
I have family members on Linux, once I've gotten them set up I rarely do tech support. The setup is the hardest part.
But some of that depends on how a computer is set up, I know how to set up a Linux distro where I know it will be stable. That's where new users sometimes fall over. Having anypony around to help bypasses that.