I think it's going to be a long slog. Even though code is made modular these days, this stuff has got to be looking like spaghetti here and there at this point. Pull one end, they may have no idea what's going to happen somewhere else along the line. If we're lucky, it's not us making those discoveries...
Some of the changes I don't mind too much although I'm still not used to them. I mean it does makes sense to carve out tabbed views of movies, say, vs. music. You want to see different attributes in the main window in the list view. Playlist vs music still trips me up though.
Various other changes in the past few years I take a pretty dim view of. Bring back multiple playlist window editing! And I will never forgive their taking away by-the-playlist options to shuffle and repeat. Likewise, option-shuffle, and visual resequencing of shuffled lists.
I still like being able to flip into the store from iTunes, and to be able to see my purchase history with a few clicks. It beats poring through archives mumbling "I must have that receipt here, didn't I buy that track... did I rip the thing??"
So I'm not giving up on this ecosystem for my music. I'm a little cautious about running the updates though. I wait a little while. I make assorted backups first and also ensure I have some independent external archives of both the libraries and the underlying data files first.
Wait—are you saying that you can't shuffle a playlist? That's how I listen to music! No way I'm updating if that's the case.
Maybe I misunderstand you.