I know a lot has been said on the subject and I've said a few things myself. However, I've about reached my breaking point and would love it if someone could point me the way to someone at Apple to talk to. I'm referring to syncing and the dreaded message generally at the end of the sync, "waiting for items to sync." Sometimes the message will end after a long time (an hour) and all will seemingly be ok, and sometimes it will continue indefinitely. I've tried virtually every suggestion here and from apple senior support. I have had the same problem for well over a year with 2 iPads and 2 iPhones. I've had syncing problems seemingly forever, back to 3 years ago when I had a MacBook Pro and after with my present computer, an iMac. However, the problem was not the same previously, i.e., waiting for items to sync., in the past year or so. It seems to be happening with more regularity now, like almost every time I want to completely change songs on my devices. If I interrupt the "waiting for items to copy," I often get a huge amount of "other" indicated in the bar graph in iTunes showing the amount of audio, apps, etc. I have a large library, almost 2TB and 80k songs. I don't know if that's the problem. I also have a 124gb iPad and 2 64gb iPhones. I rotate the songs every few weeks... I have about 15 playlists set up randomly so I can just switch playlists. As a result, I can rule out that corrupt songs are causing the problem unless there are a lot of corrupt songs. Without exaggeration, I must have talked to 10 senior apple technicians. I'm covered by Apple Care on all but one of my 3 devices. It's always a very lengthy conversation and doing mostly the same things over and over with call backs necessary. And the problem doesn't get resolved. The only way I can seem to resolve the issue is by doing a complete erase on the device and syncing my songs 1 playlist at a time. It's an incredibly lengthy process, especially when I try to sync normally at first and that fails - there went up to a few hours' time. However, I'm not so sure about this method any longer. I sync'd my iPad yesterday, which took an entire day or about 15 hours. After completely erasing everything and restoring, I sync'd 1 playlist at a time as previously mentioned. I got the "waiting" message after each sync, but it eventually went away and all seemed fine. That is, until I checked my iPad. I should have had 22,000 songs (according to iTunes and a manual count of songs taking the totals from my playlists) but the iPad indicated only 12,000. If it is not an inherent problem with every version of iTunes and/or every OS in the last few years, the only other thing I can think of is that's my computer. I am flinging my hands up in the air at this point and begging for a phone number of someone to talk to who can help. Most of the senior iTunes reps claim they are unaware of the problem, which is baffling to me.