Ok, that was a (partial) waste of time. The first 500 pictures went ok, then I added a few more folders, about 700 new images. It fialed but at least itunes gave me some feedback- the sync was interupted (or words to that effect- I made the mistake of de-selecting one of the larger folders before writing down the error). It is working if I keep the batches very small (typically less than 200mb).
7/8/12 at 6:25am