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No, you are absolutely right. When cats over groom, it is usually a medical issue - NOT a behavioral one!
The rump area is one of the most common places to see serious skin lesions secondary to fleas.
He may have a flea allergy, which makes him extremely itchy after even just one flea bite.
What product are you using for flea control right now?
Frontline is a good product. Since he is still uncomfortable, I would consider requesting a short course of a steroid from your regular vet. His teeth cannot be filed down, but it sounds like they are extruding (super eruption).
When that happens, if there is oral trauma, etc we may consider extracting the teeth entirely.
You would need a veterinary dentist to do this. The reason is that the enamel is not that thick. Drilling down the tooth with expose the pulp, which would require capping the tooth. It would be easier and less expensive to extract them.
Sorry about that, I had to step away. Yes, the steroid injection or preferably an oral pill would be best to give him relief from itching.