When really what I wanted to do was just listen to music while I'm walking around, and have a limited amount of worrying when it comes to getting music onto the device. (IE, it Just Works territory) My behaviour is now circumscribed in other ways - my attention is split between things I really want to work on and this malaise of I ought to be crafting better tools to work with my music player.
"You can just set up rsync once!" is kind of a non-argument response to this - an Apple gadget, in this case, I set up nonce. Plug it in, it initializes, and syncs everything. Now I can listen to music where-ever I happen to be, and I don't have those circumscriptions to my attention.
If my Apple device annoys me sufficiently that I really want to have that level of control, there's a myriad of devices out there that automount as USB devices, that I could set up all sorts of nifty on-insert rules and script to high-heaven.