Photos won't sync with iPhone

Hi there,
I often have the situation where the sync on my (1st gen) iPhone will fail when trying to copy photos to the iPhone - the error says that it has failed as there is not enough free space on the device.
The phone and iTunes both report approximately 100MB free space, more than enough for the few photos (all scaled down to 800x600 anyway!) to fit on.
I have tried deleting all the photos off the iPhone and re-syncing and that still fails.
On the odd occasion it will work!
I can fill up my iPhone with video/music (i.e. take it to zero k free space) and I USED to be able to do this with photos, but can no longer do it.
I am using iTunes 8.2.1 on OS-X (10.5.7). I'm using iPhone 3.0 software on the iPhone
I have a folder called 'iPhone photos' and folders in that with all the photos I want to copy. All these photos are re-sized to 800x600. I use the 'select folders' option to select which folders I want to sync. There doesn't appear to be a specific folder that causes/resolves this problem.
Any ideas?

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Photos won't sync with iPhone

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