Linux

I've been using Linux for so long that it's hard for me to give an approximation of what a new user might find challenging, but I think that something important to remember is that computers are hard. I've spent my entire life studying computers and I'm still learning every day.

Most people grew up with Windows and learned how to use it over the years, but remember that it took years, and most of them still aren't very good at it. Linux requires different knowledge than Windows, but it doesn't inherently mean that it's harder. If everyone grew up using Linux we wouldn't hear about "how hard Linux is" but instead about "how hard Windows is".

At least when something is broken in Linux, it probably has a cause (usually the user) and solution, and a way to debug what happened. When something breaks in Windows you've got about 3 things you can try before the solution is to reinstall.

As for solutions, I don't know if there's a certified pathway into Linux - I think installing something like Linux Mint and just using it like a computer would go a long way towards getting you comfortable with how Linux works without forcing you to study. Once you're comfortable using the GUI, you can take a peek behind the scenes at your leisure - there is documentation everywhere for everything on Linux.