Quite interesting to see how our experiences differentiate as I never got the chance to really understand what I was doing or what is going on but maybe that depends on our different approaches when switching distros
It ultimately comes down to workload, I suppose. If you're a creative professional or build iPhone apps for a living, I doubt you'll enjoy your time on Linux very much. As someone who does neither of those things very often, Linux feels like home to me.
I also think it really depends on what your end goal for doing it is. Do you just want to get to the point where you have a working dev environment as quickly as possible or do you want to learn about Operating Systems and hardware for its own sake. For me, at the time, getting NetBSD working on a 'no name' PowerPC dev board I bought off of eBay was a fun goal in it self.