Why do some but not all podcasts transfer to my iPod Touch

I manually drag/drop podcasts to my iPod Touch. If I select a set of them and drag/drop to the iPod Touch, most will transfer fine, but some will not.
I have lots of memory on my iPod Touch
Some characteristics of the podcasts that do not transfer:
1) The podcasts that do not transfer cannot be transferred individually either.
2) They play fine in iTunes.
3) They tend to be in contiguous blocks. E.g. all prior to a Nov29 transfer, the podcasts between Nov29 and Dec 15 do not transfer, and all after Dec15 transfer fine.
It behaves like the system incorrectly thinks that they are already on the iPod Touch, and therefore does not think they need to be transferred again.
I have tried marking them as "played", and then marking them back to "not played" in iTunes no effect.
iTunes 10.5.1
iPod Touch 4th generation w/software 5.0.1

Flash drives typically are formatted FAT and hold a very limited number of files. You can overcome this by exporting the photos to a folder and dragging that folder to the flash drive
You know don't you that moving the photos in this way loses versions, faces etc. generally it is better to move the iPhoto library intact to the new computer (network, external hard drive, direct connection, etc)
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