I was forced to upgrade to the latest version of iTunes because I bought a new iPod Touch 4g. I also own an iPod Touch 2g, which did not require the latest version of iTunes to sync.
About half of my photos could not be synced in the latest version of iTunes, although the previous version had no trouble reading and syncing the same files to my old Touch.
I contacted Apple support, which not only did not help, but failed to call me back as promised after suggesting a procedure that would take at least 45 minutes to complete.
I wound up solving my own problem eventually. What I discovered was that for unknown reasons, this version of iTunes could no longer read certain TIF files created in Paint Shop Pro. The solution was to resave all the files using Photo Shop Elements. I made no changes to the files and saved in the same format, but suddenly iTunes was able to read them and sync to my iPod Touch. (As suggested elsewhere on these forums, I did have to remove the photo cache to get this to work. However, just removing the photo cache did not work; I had to resave the files first.)
Beware, apparently a TIF is not necessarily a TIF! I have no idea what the difference is between the Paint Shop Pro TIF and the Elements TIF. Elements did not have any trouble reading them. Maybe Apple could address this problem in an iTunes update? It is very inconvenient to have to change my workflow to get my Touch to sync my photos.
