I think perhaps you missed my point on the multiples. I just searched my forum posts for "/2007/01/1.jpg" which should yield at most a few copies of the same image in related posts. Instead it returns 558 hits in a total of 371 posts.
I don't see any way for this to occur without an indexing error in the software. I think it is at least worth a look at the arbitrary name generator and where it stores its counter.
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