Issues with photos/videos not uploading in chronological order..

I have been having issues with Adobe Bridge not uploading my photo/video files (from a CF card) in chronological order. When uploading I select to rename the files by shot date + 01.. etc. For photos the first image then becomes the last image after uploading, and for video files everything is out of order. Not sure why as the only other thing I have selected to add is copyright info. Also having issues with Bridge not converting raw files to DNG (which has led me to use Adobe DNG Converter - not terrible, but hopefully there is a reason?). I think it is a problem with Bridge, as photos uploaded to my website - something completely non-Adobe related are also then thrown out of order.. so it seems to be an issue with files that have come through Bridge at some point. Any advice is much appreciated.

I just noticed that iTunes is now accepting 'some' videos. They are all the same file type (mp4), but iTunes is just randomly choosing which videos it wants add to the Library & not.
I'm still not getting any results when it comes to the Photos.
... and one last thing ... only random songs are displaying the album art on the iPod. Yhey ALL appear in iTunes. If i restore my iPod & re-load everything, some of the songs that DID have artwork appearing on the screen now don't.
This is really messed up! Wonder if the eventual Vista-compatible iTunes will fix this problem ...

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