Personally I haven’t. While Linux is imperfect, choosing the right distro makes the rest of the experience straightforward. And with it’s whole complexity, I find Linux more user friendly than Windows. Even driver issues, broken shadow file ownership and KDE specifics only made me more confident about my choice to use Linux after I solved everything.
I am not sure whats to improve, it is just a situation where it is easy if you know how.
As for the iphone, the amount of trouble that process has caused me is not trivial. Things are not the same! I would put it as more complicated. People are just used to dealing with it. Part of the issue with the iphone is applications and Icloud crap.