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.
Ah yes I did it like that before. At home it’s not a problem since my NAS is always connected but taking my laptop outside would be problematic unless I had the VPN enabled.