Initial sync worked as expected. Subsequently added some new folders from iPhoto to sync as well and they don't appear on my iPad. They are in iPhoto, they are jpgs. I'm syncing to a MacBook Pro.

There are about 1400 pics selected and I have varied the selection with the same results. When iTunes reaches the photos it always says "optimizing x of 355 photos for IPad". It goes through once from x=0 to 355 then begins again with the same message, a new status bar and goes through 0 to 355 again. It then says syncing photos and the sync ends without an error message. However, when it is done all the same photos are on my iPad and none of the new photos have synched.

I turned photos off, it went through the same process and did empty the photos from the device. I then resynced with the photos I wanted selected and only the old photos reappeared. Tried tossing the iPad photo cache, same result. Any suggestions?

It might be a filename or folder name that it doesn't like. Check what the 355 or 356th photo is in your folder and see if the name has any special characters.

It also could be a corrupt file. Try getting rid of the 355 and 356th photo to see if that helps.