Problems transferring photos to iPod from Nikon D70 and Finepix S602 Zoom

I've been having some difficulties getting a clean transfer of photos from both the D70 and the S602. (Yes, I know the latter is not on the supported list, but the D70 is.)
The first couple of attempts worked fine (both on S602). Transferred 16 photos (9.8 MB) and 13 photos (15.2MB). One from a CF card and one from SmartMedia.
However, the third time it went wrong and not only did the transfer fail but all previously transferred photos apparently disappeared.
Short panic and one reset later the photos are back, but the third roll a) claims to contain only a subset of the photos and b) isn't browseable. Delete is the only option. Further attempts have the same problem, but manually stopping part way through is more successful, so I was able to deal with it in batches. But this is a real pain.
Same problem arises with the D70. But with a 1GB CF is even more painful to manage.
There seems to be little consistency in how much can be successfully transferred before a problem arises. Sometimes it is breaking after 15 shots and a few MB. Other times I can get more transferred, for example, 101 MB (38 photos) or 61 photos (60MB).
I tried switching the D70 to PTP mode (the S602 doesn't support that) and had more success. Everything was going well until it hit 118 photos (299MB) and then it stopped, with the 119th photo showing up as a question mark. This is repeatable. No need to reset this time, so I wonder if it is the same problem.
All the photos successfully transferred are accessible from the PC, but it would be really nice to get it all working more smoothly. Any suggestions?
Windows XP

This is weird, when I connected the iPod to my computer it opened iTunes, and I had to do all the stuff you do the first time, but this time I checked 'Automatically add photos' or whatever as well. So, then it started to put them on my iPod but I pressed skip because I didn't want like over 770 pictures on my iPod, just the ones I would pick... so then, it updated the songs and everything, that was great but I got my hopes up too soon and figured I'm in, but no, I still get the same message when I try to upload photos... ahh, please help!

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Problems transferring photos to iPod from Nikon D70 and Finepix S602 Zoom

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