Note to teh interwebz: iTunes 10.2.1 and 10.2.2 (at least) on Mac crash when trying to sync some JPEG2000 files from a Mac to an iPad (first generation iPad).
I tried to sync some old maps of Boston from my Mac to my iPad and iTunes 10.2.1 and 10.2.2 crashes every single time while trying to “optimize images” during the syncing process. I assume that means that iTunes converts (or at least examines) all images it sends to an iPad, and iTunes really didn’t like that particular JPEG2000-formatted image. When I deleted that image from my pictures-to-sync directory iTunes completed the sync just fine. When I put the file back in the pictures-to-sync directory iTunes crashed.
I filed a bug with Apple.
Hopefully they fix it. Even if JPEG2000 images aren’t supported on the iPad (which I found out they aren’t), iTunes shouldn’t crash when processing them.