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.
With Linux itself or with the broader realm of ‘Linux software’?
By itself, Linux is a fantastic family of operating systems. Has never failed me and probably never will. At least not until I care enough about differences in userland handling in Linux vs FreeBSD, for instance. And even then, I might just switch out of preference, and not because one or the other disappointed me.
As for broader Linux software, or GNU software, or just FOSS in general - by far the biggest potential issue is probably systemd, and it’s still meaningless for the vast majority of users. Other than that, my personal biggest issue was Hyprland breaking completely after updating. But it’s not a super major issue, because I can just use Plasma instead.