I have Cover Art for all of my songs in iTunes, yet Media Sync only brings over some of them. I have ample space on the media card. Is there something I need to verify or change in iTunes so the missing ones get transferred?
on an audio file, the cover art is stored within the id3tags of the music file. there are some formats for id3tags. For the old format (ID3v2), the cover art is stored in a field called PIC. the v2 format has deprecated and replaced by a newer one. in the new format, the cover art is stored in a field called APIC which is better (mainly because you can store PNG). Unfortunately, Apple iTunes uses the deprecated format.
what you can do is use another music file management software to add the correct APIC field. You can use tag&rename (there's a free full trial) or Songbird (free forever). When the APIC field is stored, the magic is that iTunes can read it too.
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I figured it out, too. I got a utility that reads the cover art for each music file in iTunes. Apparently, there are two types. One type is downloaded and the other is embedded. Only embedded ones are brought to the Blackberry. I had a mix of them, though I don't quite know why. The utility took all the downloaded art and embedded it. I then re-synced the Blackberry and it worked great!