@jonas I think you are misunderstanding the issue. Here's another example extrapolating from my last update.
I have copied all of the music files from a folder on my hard drive to the current playlist using the "Replace current playlist" context menu option from the files view. There are no cover images in this folder. I randomize the order with "Ctrl+H". The first song is Tie A Yellow Ribbon by Tony Orlando & Dawn [TO&D].
I use the "Edit track information" menu item context menu to navigate to the "Summary" tab and from there to the "Change cover art" menu to look up the cover art for this song. At this point it is displaying the symbol Strawberry uses when there is no art associated with a song. Having found a suitable image, and watching the displayed image change from unassociated to the cover art for this album, I click "Save".
Unfortunately, now most of the rest of the files in this directory show the exact same image I had associated with that song. on most other songs. There are a few songs that have their cover art embedded, these seem to display correctly. Everybody Wants Some by Van Halen's, Women and Children first album shows the TO&D image. I skip ahead and using the same process mentioned above I set the cover art on a dozen or more songs from various artists. Lisa Loeb's Bring Me Up from her Cake and Pie album, Chicago's Look Away, from their Chicago 19 album, Big Deal from LiAnn Rime's self titled album. They all look correct.
Unfortunately, when Strawberry begins to play the song, it will often revert back to the same TO&D image. While listening to Shakira's Ojos asi from her MTV Unplugged album, I reset the image to the correct cover art and away from the TO&D image. It updated in the lower left hand corner, and in the notification area. When the next song started I decided that I wanted to hear that song again go I told Strawberry to play the previous track by selecting the "Previous Track" option in the context menu from the notification area. Guess what happened? When it started playing the Shakira song that I had just corrected the cover art for, it once again displayed the TO&D cover art.
Are you saying that there's no way for Strawberry to correctly associate cover art with song files when there are song files from multiple different artists/albums in the same directory?