Back to the original topic of how to use a $500 voucher.......
Could you pretty much put together 2 round trips in the same reservation?? Imagine something like this: LAX to EWR to ONT to LGA to LAX. If each round trip NYC to LA area would be about $250, I think the whole thing would price close to $500.
I wonder if you could even do LAX-EWR-LAX-EWR-LAX in the same reservation.....