Album Art Won't Stay Attached To This One Song File

Hello community,
Out of the 4172 songs in my iTunes library, for some time there there has been one song which will not accept any form of album artwork. I add it and hit "OK" and it goes on the song, but as soon as I switch to another song and back to this one, the artwork is gone again. The entire album (as with most of my albums) is 44.1k, 16bit AIFF files. I have not encountered this problem with any other song. Only this one. No matter how many times I duplicate into an entirely new file, I still can't add artwork to it. This problem was annoying me greatly until I converted the song to a similar format, Apple Lossless, and now it freely accepts the artwork, and the artwork stays. But as soon as I convert it back to AIFF, the artwork disappears and I can't add it. I even attempted to re-rip it from the disk, converted it through FLAC, ALAC, and then to AIFF, the first two of which accepted the artwork, but not AIFF.
So my question is, what is wrong with this one particular song not accepting album art solely when in the AIFF format? It seems very odd to me. Any help would be appreciated, because now I have a standalone ALAC file in my library and it's extremely annoying to think about. >.<
I should also mention that this has been happening from Mountain Lion, through Mavericks and now onto Yosemite. Don't even get me started on how the playback buttons only work once. That's a whole 'nother issue.

For #1, the iPod's Artwork cache does get corrupted when making frequent changes. In the iPod's Music preferences tab in iTunes, remove the check beside "Display album artwork on your iPod" and select Apply.
Once the iPod has finished syncing, recheck it and hit Apply again. iTunes should recreate the artwork cache and re-sync it to your iPod.
For #2, are you running the itunes database (it has an ITL extension) from the exHD ? Or from the default location on your C: drive. The downloaded artwork from the itunes store goes into a folder named Album Artwork, and that is created in the same folder as the ITL file.
Not sure if this is it, since I embed the artwork in all my files.

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