ITunes randomly linking to non-song files... a real curve-ball of an issue

I have been having problems with songs in my iTunes library suddenly not playing. When I select "Reveal in Finder" the file that it revealed is often a driver in my library - worse still, the song is then no-where to be found using spot-light but it can be manually found in my iTunes library.
If I re-import it back into iTunes, it still cannot play. Reveal in finder takes me right back to the same driver. In the finder it looks like this:
This happened before and I rebuilt my iTunes library but now it has started to happen again.
My library is on an external drive. I have run a disc repair to fix permissions on that drive to no avail.
It seems to be random in terms of what songs this happens to.
It is also happening to Podcast files although in that case they tend to link to single audio samples that i use for unrelated audio work - such as a single horn blast etc.
I suspect that this might have something to do with a secondary external drive that I hook up on occasion for time machine syncing. This is just a hunch.
Anyone have any thoughts?
Thanks. Doug_
Message was edited by: Douglas Suiter

I have also noticed that the affected songs will play in Quicklook from the finder, but the cover art is missing. For example, I have the sound track to the Piano but three songs are affected by this issue, as illustrated below:
Message was edited by: Douglas Suiter

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