IOS5/Itunes 5 sync issues - music greyed out, not syncing across

Question

Hello,
I am having issues syncing music from iTunes to my iphone and ipad. I use autofill, but have had the same issue when using the sync all music option. All the files are listed in the music tab under the device, but half are greyed out and unplayable on the device (they are greyed out on the device too). There is a sync icon next to the files, but clicking on it does nothing.... I did a clean restore to ios5 and it copied my apps over, but none of my music, pictures etc. This is really annoying can anyone help?
IOS5 GM
Itunes 5

Answer 1

I have been fighting this problem with both my iPhone, my partner's, and my nephew's. It seems to have something to do with music purchased in iTunes vs. music that is ripped, since all my ripped music transfers fine and stays put.
On the other hand, downloaded content shows up doubled (one black, one grey) when I look at my music through the iTunes, just like that screen cap. As long as there's a "black copy" showing, it plays fine on my iPhone 4s, but I find I have to remove the greyed out copies manually and then manually transfer from my iTunes library or from the purchased option on the phone itself. In other words, if the music on the phone in only greyed out copies, and it's not on the phone, it doesn't transfer manually unless I first delete the greyed out versions. -- And then the greyed out versions magically reappear after it contacts the cloud and backs up.
I also sometimes end up with doubled copies, and my albums don't all sort the way they should -- so for example some Diane Schuur shows up under the artist name, and some shows up under albums. To put it all together I had to make a playlist, which is stupid.
Finally, there are some 46 items it tries to sync everytime I do any wi fi syncing of anything with my phone. I have no idea what that is.
I'm tempted to wipe and let all iTunes content be restored from the iCloud, a process that would require an overnight restore. I'm guessing that might solve the problem, but why should it all be this hard? Does Apple look at these comments, because I notice there are several different threads on this site concerning the music app and the iTunes/syncing issue?
Bill