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.
A little I guess. When I had finally convinced my dad to try out a dual boot, and was trying to install it for him on his new Threadripper system, it failed. The platform support Threadripper wasn’t ready even though it had been out for at least a little while.
But I don’t remember the details it has been around 8 years. Nowadays I know to confirm these things first, so in a sense it was my own mistaken assumption. But still it fits the question because at the time I was disappointed.