Basically the driver was that in college and shortly thereafter, I had more time than money, so it was worth it to use an OS that required an investment in time to make it the way I like.
Now that I'm older with a kid, I have more money than time, so I'd rather have an OS where I can solve my problem with money.
I'd actually rather still be running Linux, I just don't have the time. :)
Just one man's experience, but if you want a Linux that "just works," try Mageia. I've been running it since 2011, and in that time I don't remember ever hand-editing a config file. All my laptop's hardware works, printers just work, I use KDE and the monitor hot-plugging just works, the whole nine yards. It's pretty sweet!
It's actually gotten to where I no longer really remember how to do anything in Linux that would necessitate dropping to the command line. Happily, I can't remember the last time I needed to.