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Import log - 500+ tracks not imported from itunes

Hi all - hoping for some help or guidance please.

Im a mac user and I recently created new sync file on a USB stick, importing playlists from itunes. Typically one or two tracks don't import but this time round its pretty much everything (hundreds of tracks according to my import log file). 

Ive had the standard message:

One or more files were not imported.
Track(s) were not imported due to the following possible reasons.
- The file path is longer than 255 characters.
- Invalid file format

I suspect its due to the characters however there are some glaring inconsistencies.

I recently moved from an old mac to a new mac, and it might be that the file paths are a bit longer - but nowhere near 255 characters. As I'm dealing with hundreds of tracks, is there a simple solution to fixing this please ?

Simon Bromwich

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