Linux

The sky-high barrier to entry was a MAJOR problem for me.

When I was seriously considering installing Linux, the first issue I ran into was the lack of tutorials - or, more accurately, the bewildering array of tutorials. You couldn’t just search the term “Linux tutorial” and expect an answer that was specific enough to your case to actually be useful. There was (and is) a wide variety of distributions, each with their own unique behaviors and requirements.

If you were looking for help with the Windows or Mac OS, all you needed was the OS version number, plus maybe some basic hardware info, and most of the time you were good. With Linux, answering even the simplest question required a focused, concentrated effort, and there was still a decent chance a beginner wouldn’t have enough background knowledge to understand the answer. Generally speaking, beginner-friendly tutorials were often too broad to be useful, and specific tutorials tended to assume knowledge that a beginner didn’t have.

Unless you had someone standing by who was willing to be your Linux Yoda, starting out was very difficult. I didn’t know such a person, so I just gave up.

Granted, this was several years ago, and things may have changed. I’m speaking from my own limited experience.