My impression is that iTunes doesnt bother to read exif data at all.

Yeah, batch processing everything sounds like the only solution.

If someone made a third party photo uploader, maybe that would be a solution. Actually someone makes something called photopod but it doesnt support this device and its rotation feature is the opposite of what I need.

Since batch processing and rearranging my collection is out of the question at the moment, I guess this thing I'd still just a web browser.