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.
The one recurring unsolveable problem I run into is not being able to kill a process that’s stuck in D state. If something has broken in the layers between that process and hardware (not uncommon when working with old cheap “box of scraps” hardware, as I like to do), it can get stuck forever and you have to kill the whole system, sometimes forcibly. Not the end of the world, but it sucks when it happens.