Yes - it does mean all or nothing. You must hit 27 flights.
Though I don't agree that it rewards people who travel less. They look at your travel history and set the bar a little higher than your typical travel to get you to fly a bit more.
Originally Posted by CO_Nonrev_elite
I live in Houston and I got it, although I am still wondering if the deal actually means that I have to fly 27 roundtrips to get anything at all. Would seem odd if it is an all or nothing type deal. This would suggest that they are rewarding those who fly less much easier.