The biggest hurdles I run into are relating to software management. People expect to google up a .exe and run it.
What ever happened to those "download in ubuntu software centre" orange buttons I was seeing around? That was a damn good idea to bridge the gap while bringing users into the fold by making sure apt is aware of the program being installed, and that it's installed via official channels.
Does Mint still ship gdebi or whatever it was called?
Oh and don't get me started on snap. I always tell people to disable snaps from the software centre if they're installing a *buntu.
Sorry if I misread but it seemed to me like you were the belligerent one first. Maybe I was just poised for it after the first comment in this thread.