Photos not syncing with iPod touch

I've been having a weird problem when syncing photos with both 2G, 3G and 4G iPod touches for the last 8 months or so.
Photos that that were taken in a portrait (vertical) orientation using my Canon camera (and synced with iPhoto - currently at v. 8.1.4) are being synced with my iPod touches without any problems BUT photos taken in the landscape (horizontal) orientation are not being transferred to the any of my iPod touches.
It worked fine for years but all of a sudden, the problem appeared. When I sync in iTunes I get an error saying that 'Photo named xx could not be transferred' (or something like that). The message appears for one photo but the problem affects an increasing number of photos (any photo taken since the problem started).
If I edit the landscape photos in iPhoto and change something about these photos (e.g., crop them) then they sync no problem.
The photos taken (and stored in iPhoto) before this problem started are still being synced with my iPods without any problems.
Is this a glitch with the Canon camera which is somehow corrupting the photo's meta data? Or is it a problem with iPhoto or iTunes?
Any insight/assistance is greatly appreciated!

I have a similar problem with my iPod touch (I think 4th gen, it's software 4.1 anyway)
Sometimes when I sync it comes up with a window saying "no photos were copied to your iPod because there is not enough free space" even though there clearly is. The bar at the foot of the window also indicates that there are photos on there as well. To get round this bug I have to delete some music files and re-sync.

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