Yes, I've been using the wrong word all along. It's not a playlist issue... it's probably some kind of corrupted metadata that Itunes creates when it imports a song file. The metadata is not in the song file itself or my CRC checks between my active song files and my backup song files would not have matched.
On the surface, the problem you're experiencing seems different from mine and at least one other poster. That poster indicated that his files are cutting off after 4:10 of play in Itunes, just as mine were. Also, when my songs cut off, there was no silence, as is happening with you. Itunes immediately moved on to the next song.
But, you're not experiencing any playback issues with Itunes, but with your synched devices. So that changes things a bit.
"It cannot be overstated that the same song is fine as it exists on my home computer in Itunes as is every single song existing there."
Okay. So, Itunes is playing the songs correctly. Since it's happening across multiple devices, though, and since the common denominator between all the devices is that they're being synched by Itunes on your computer, it's pretty safe to say that the problem is with Itunes, not with each individual device.
My next question would have been to ask if the songs are cutting off at exactly the same time on all devices, but you've already answered that question. You said your Iphone is cutting the Moody Blues song off at the same time as your Ipad. This is now a powerful indicator that the problem is with Itunes.
It all keeps coming back to Itunes.
Proposed solution: Do what I did to resolve the issue, then re-synch the devices. Delete one of the problem songs from your Itunes library, choose to keep the file, then re-import it from its original location on the hard drive into Itunes, then re-synch your device. Let us know what happens.
-Paul