Thanks to taking the time to write a thoughtful answer, @beanz - you bring up some really good points. Somewhere there must be a "complexity vs. functionality" graph, where Apple products tend to find a sweet spot for maximizing capability with simplicity.

But along with that is the decision, as you point out, of weighing benefit vs. effort. I guess like many things sometimes it's hard to see "why" so we're less willing to deal with a painful looking "how." Sometimes what helps is finding people we enjoy being around, as we get over the learning hump.