I know it's not a play count issue, I've just been following a few Apple discussions about the overall change in functionality (for me) and I happened to reply to this one without realizing it was specifically focused on play count sync.
I saw your post about this on ilounge yesterday and I almost replied "noooo, it hasn't been broken for ages" but then I realized there seem to be so many variations of this problem that different people are having that you're probably right and it was broken back in iOS3, so I didn't see the point in starting up a back and forth about it.
How funny to find you here as well.
You are exactly right, I have always managed my music, and it did used to work up through iOS4; going back to my iPod Photo 60GB from 2004 (2005?) and my first iPhone 3G, it had always worked. I'm really sorry other people have been dealing with this longer.
How utterly stupid and pointless is a "Live Updating" option if it's not even remotely live at all? Having to be at home, connected to a computer by a hardwire connection (or I suppose with iOS5 through wi-fi) just so a mobile device can be made aware that it has been playing songs while away from home isn't really my idea of "Live."
For that matter, why is "Live Updating" a preference that has to be enabled? Why would anyone not want playlists based on play count or last played to Live Update? That's the entire point of using that kind of data to generate a "smart" playlist in the first place. It seems like the kind of thing I should have to hack into through terminal to turn off, not a checkbox to turn on (which obviously still doesn't work).
And what kind of sense does it make to take a broken functionality that was afflicting a portion of iOS users and, with iOS5, inflict it on everyone? I'm sure that wasn't a conscious decision, but it's definitely been the result.
Especially frustrating is the infrequent, random times everything works like it used to for no apparent reason. Like yesterday when backing up/syncing, everything I listened to since Sunday suddenly was all there with correct last played dates; but before the data starting on Sunday it said I hadn't listened to anything since March 27. Or like the time I dragged my laptop and iPhone to the Apple store to talk to a real live person about it and everything worked perfectly. Perfectly! Several times of plugging in and unplugging, syncing, backing up, different playlists, and everything worked exactly as it used to. I'm sure the guy must have thought I was a crazy person with an imaginary problem.
Anyway, it's partly reassuring to know that this is expected behavior and at the same time really disheartening to know that it's been broken for much longer than six months and Apple has done nothing to remedy it. I sent in another Bug report about it this afternoon. Maybe I'll just start sending one every day, I suppose it's my only recourse to try to get something done about it.
Wow, that got a little more rant-y than I intended Sorry.