Good news (at least for me)! Both 103.5 and 107.9 allowed me to pick up the prizes that I won recently even though the waiting period had not ended (see my previous post here). My guess is that most stations don't even check to see when the last time someone won was (and I'm guessing other stations just don't care). Looks like the waiting period may just be a formality. Time to press my luck a bit and see if I ever get turned down.
P.S. The opera turned out to just be musical theater and it was fantastic. The dinner, on the other hand, was just a $10 gift certificate. Oh well, can't argue with free.
