Will add to this horror story. I have a 3-month old iPad 2 and a 4G iPod Touch. I upgraded my Lion and iTunes with the latest updates, and I replaced my old iPhoto with iPhoto '11 before I started this odyssey, thinking i wouldn't have issues. Loaded up iOS5 on my iPad, worked like a charm. The next day, I added iOS5 on my iPod, and tried to sync, and it crapped out. I couldn't get Music, Photos, Videos from iPhoto, Voice Memos or Audible Books. Read all these posts about people having problems, and tried many things, but could never get everything on and synced. Went through restore several times even. Even wiped the slate clean and started as if i had a new device. I eventually got everything but Videos from iPhoto, Voice Memos and Audible Books. But only by sycing each file type individually through the sync process - 4 hours.
After a full day of misery, i wanted to make sure new things would sync, so i got a new app, took a few photos, bought a track of music, added a video. Tried to sync my iPad, which was perfect, and low and behold, it crapped out - even lost the Audible books AND videos from iPhoto that had loaded FINE the first time (the biggest mystery of all). Ended up going through the same misery for a day with it. Finally managed to get everything but Videos from iPhoto, Voice Memos and Audible Books. But only by sycing each file type individually through the sync process - 4 more hours. I tried to sync the new files I added, and the only thing that synced was a new podcast I had no interest in.
Got fed up and called Apple. One of his first suggestions was to use the Kindle App for my Audiobooks. I asked him if he thought Steve Jobs would like that suggestion. That ended that discussion. He took me through the same crap I had already gone through over two days, though one suggestion wiped out my photos and cost me another 4 hours of misery. I will enter my third day with Apple later.
I've restored, I've started as new devices, I've gone incrementally through the sync process, I've backed up to the cloud vs my computere, I've synced tethered and wireless, I've tried changing my MOV files to mp4 and i tried redownloading audible files as lower quality, but the same problem.
So, to date, my situation is:
1. I can't get three file types to Sync: Videos from iPhoto, Voice Memos and Audible Books
2. I can't get ANYTHING NEW now onto my devices through the sync process - except podcasts. I can download iTunes purchased files through the iCloud, but that's essentailly a work around.
I have my original iPod white brick - the first version, every version since, plus a few extra for ones I dropped or got stolen. I have been using Macs for ten years. I have upgraded operating systems too many times to count. I have never experienced such a co*k-up. If I wanted brain damage like this, I'd have bought an Android phone and a PC.....
Will advise if Apple comes up with a solution.
Irritated beyond description...Sigh