Re: It took until now?
iTunes is bloated and slow, but it handles playlists very well, and the integration with the iPod hardware/software means that sync'ing is quick [*]. It also facilitates 2-way synchronisation (i.e. I can tag songs on the iPod, and iTunes will pick those tags up); handy for eliminating unwanted songs from a playlist over time [**].
Then too, the non-touch iPods have another advantage: physical buttons; you don't need to turn the screen on, nor do you even need to look at the device to perform basic tasks such as skipping tracks or increasing volume.
I will grant you Apple is probably ahead of the game in halfway-decent playback software, but that's solvable in the Android space, *especially* if you could have a device with an AOSP-based firmware without all the built-in GoogleCrap(tm) (who thought it was a good idea that media should continue to play even after you close the app? It must be an OS-level defect, as ALL media players do the same dumbass thing).