"...One thing I have noticed is the number of posts by veteran users of linux in many distros that are almost constantly having to fiddle with their distro to keep it like they want."
That line jumped out at me from the OP in this thread. I don't think "have to" is correct; it's more "want to". "Let's see what that option does. Nope, don't like that, let me switch it back".
My experience has been that once you pick a distribution, you can pretty much just stay with it, just doing the updates once in a while. Any of the *buntu LTS (Long Term Support) based ones are pretty much install and go. Look at the default user interface to pick which one you want, then decide if you need 32 bit or 64bit. From what I've seen updates from a distribution have a much smaller chance of breaking things than updating in Windows; I don't think I've heard of an update leaving a machine unbootable.
Then you have folks like "wizfromoz" that at last count has something like 1024 distributions installed across 64 machines or something. Does he "need" to do that? No, he's doing it for intellectual curiousity (probably because someone said he couldn't install every single distribution) and he's learning from every one of them (and graciously sharing his experience with the rest of us).
OP: it will be as easy or as hard to learn as you want it to be. Think of it like learning to speak another language: once you learn to "think" in that language it's easy. Trying to translate in your head makes it hard.