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 biggest thing I fought with since getting started has been audio. First figuring out how to make an Elgato device cooperate (not exactly the most linux-friendly company to say the least), then setting up virtual sinks and routing everything appropriately, and finally getting my mic to not sound like actual garbage.
Frustrating as hell and a very long process to get all of that working out, but definitely learned a lot from it.