re: What’s the most valuable thing you’ve won?

By proxy, all expenses paid round trip from Biloxi to Atlanta to see Soundgarden on the Superunknown tour in '96.
Got flown up there, put up in the Hotel Nikko in Buckhead for two nights, tix for the show and return flight.
I say by proxy because one of my best friends won it, but took me along for the trip.

I personally won tix for the Black Sabbath "The End" tour in Houston in 2016...