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Maybe that's why JRiver works for me. I don't just copy files from my computer to the thumb drive... I let Jriver recode them first. I use it to normalize the songs so that they peak at the same volume level and then import them to a thumb drive. That way I don't have some songs that are quiet and some that are loud.
First, I create a playlist in JRiver with all the songs I want. Then I insert the thumb drive and add it to JRiver under drives & devices. Under the tools and options I tell it to normalize the files and to convert to MP3 variable bit rate. Then I synch the thumb drive to the playlist. This recodes all the files and then uploads them to the thumb drive. In the process of doing this, the album art goes with each file. As long as your songs are associated with an artist and an album, the album art "should" go with it. I have some songs that don't have any album art but this is because they were internet recordings I made from streaming radio stations. When I saved these songs I did not assign them an artist or album title and instead it just has the song title. Without the proper artist and album embedded in the MP3, the album art will not properly associate with the file.
So to answer your question, make sure that you have not only the correct song title, but that the album and artist are encoded as well. If these are left blank or labeled "unknown" or "various artists", then the album art will not display and you will just get the blue note.
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