Interesting point, however, is that the only major issues he had were with OBS and him macro keypad, and everything else worked for him. That is a very good thing imo. It's a testament to how far Linux has come. Now we just need to ensure all the Wayland work gets completely done across all desktops and then it's a matter of time before even stable and "conservative" systems like Debian and Mint get it all supported, at which point Linux will be ready for all, and we can move our focus to Mobile Linux and whatever else the next new big and shiny thing is on the desktop (Personally, I think the only issues after these would be making sure accessibility is all well and good, getting GNOME to finally support VR, and that's about it. I can't think of anything else).
Of course, for every story/video/etc. of someone smoothly transitioning, there's a thousand more that have basic non-starters because of certain applications/hardware, too many bugs or simply gave up in frustration.