A lot if this will boil down to what you found to be a pain. I hate to "give you more work," but do you have a list of things that you found particularly difficult?
It's death by a thousand paper cuts. No problems are a real blocker for somebody who is good with tech, but it's still more effort that I'd like to spend. I'm willing to endure that because Microsoft has become too user hostile since Win10. But I don't see how a non technical person is supposed to deal with it.
