Unreasonable space requirements for syncing photos to nano...

I have a 1st generation 4GB nano, with up to date firmware (version 1.3.1, Mac formatted). I'm using iTunes version 7.6 (29) and having trouble syncing photos (from iPhoto) to my nano.
I have configured iTunes to sync photos from only one, relatively small set, and have not turned on the full resolution copies. If I leave a bunch of space free on my ipod (over 100 MBs) then my photos sync fine. However, when there is less space free, but still seemingly enough space to fit the photos, iTunes tells me "No photos were copied to the iPod... because there is not enough free space on the iPod to hold your photos and albums."
For example, I was able to successfully sync my photo set such that I had 3.57GB in Audio, 726.2 KB for Photos, 48 MB for Other (what is "Other", btw?) and 143.4 MB of free space. However, I am not able to sync any photos when I have 3.68 GB in Audio, 47.9 MB in Other and 34.3 MB in free space.
What I don't understand is if the photos only take up 726.2 KB, iTunes should be able to sync them to the iPod when there's still 34.3 MB of free space left.

And then there were four...
This is rather frustrating. Not that I think it will do any good, but here's what I sent using iTunes' "Feedback" option since there is no way, that I have found, to directly ask the iTunes technicians a technical question:
There is no place to directly ask you (the iTunes technicians) for support about iTunes except in the forums. My question is already in the forums and already has three people with the same problem and no answer. http://discussions.apple.com/thread.jspa?messageID=6240563&#6240563
Vista Ultimate x64, HP Pavilion TX1000 CTO, 2GB RAM, AMD Turion 64x2.
iTunes version 7.6.1.9
Not all photos sync to the ipod, it doesn't say why or what to do, they are *.jpg files. Some that do sync end up looking distorted with color bars and other odd artifacts, originals remain pristine. Sometimes when syncing photos, I get a blue screen of death.
I know you don't respond to these comments, but at least have someone post a fix on the forum there, or tell me to whom I can send comments for official help with specific and real issues instead of the very general user guides, "support documents" and "blind leading the blind" forums.

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