Have you ever tried to get an early version of "S.u.S.E" working? (1998)
It's what convinced me to switch to 100% Linux and ditch Windows, so YES! 
It was actually pretty easy to install.
Getting the X environment to work could be tricky.
At the same time, it was not for the layman.
Windows was working "out of the box" quite literally.
Define "working out of the box". For me, Windows ran, but couldn't do anything without additional purchased applications. Too many applications didn't work as described, and one couldn't get a refund for an "opened package" which was a necessity to find out the application didn't work. (Actually you could, if you stood in the middle of a store and screamed at the top of your lungs, attracting a large crowd, and refused to go to the office where you could "discuss this calmly". I learned that trick from my brother in law.)

Linux, on the other hand, worked "out of the box" with my hardware, and I had lots of applications that actually did do the jobs I needed to get done. If something didn't work, it also didn't cost me anything, and there were alternatives, including the command line, which was all I had ever used before getting the Win95 machine, so that didn't bother me a bit. I just had to learn the proper specific commands, and S.u.S.E. (boxed set) came with a 500+ page book that had all the information I needed for that. I still have the book, and most of it is still relevant.
I also found I could actually contact the person who had written the broken application, or maintained it, and could get real help, if I offered to test any bug fixes, which I was happy to do. That in itself made any "extra" effort worth the time. The OS was "hands on", real people were accessible, and for the most part, friendly and appreciative that I was willing to help make their application better. I was in love with the whole concept, and still am.

Remember the free dial up disks that K Mart and others offered, for free internet connection? I had about a dozen of those and used them to discover Usenet, which put me in contact with some seriously hard core Linux users, and developers, that were also willing to teach anyone who was willing to actually put some effort into the learning experience themselves. Most wouldn't just give anyone a direct answer, but would direct you to the place where the answer could be found, and act as a guide, if you got lost in the forest, so to speak. They weren't being mean, as some people accused them of being. They were also teaching how to properly search for the needed information, on your own, so you wouldn't be helpless when they were not around. A lot of them are now gone, but every once in a while I run into one of those guys from the early days, and it's one of those warm fuzzy moments when I do.
