RE: iPod & iTunes ARGH YOU !?*/#
It could be that the colour model is unsupported, and you have to convert the photos specially. I would expect ITunes to do it for you, but maybe it's too dumb.
About the files being big, the IPhone has jpeg subsampling mening that if it's given a high resolution image it will only partially decode it to get a lower resolution rendition then work with that. The IPod might have the same processing, and if not, I would expect ITunes to only give it pictures that it can actually handle anyway.
Perhaps Itunes is having trouble opening the files and when it converts it for the IPod, it is creating a new file from one that couldn't be read in the first place.
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