It's happened to me before, minus the 7500 mile compensation.

The scary scenario is you valet check your bag on your first flight. Tag falls off, bag goes to baggage claim at your connecting hub. Bag never shows up at the valet pickup, you have a short layover--what do you do? Exit security, retrieve the bag and miss your flight, or leave the bag behind?

I know a lot of FTers go on and on about how you should *never* check a bag, but for this very reason I always check my bag if I'm on an RJ and I have a short layover.