Do the Math
I think the concept of this game is a little too confusing for many contestants and as many times as I've seen it, I sometimes have to stop myself and say "wait, what are they asking?"
Today, a rerun i think, the two trips were Italy and Samoa and +/- a thousand some odd dollars. Of course the trip to Italy is always going to be more expensive. It should be as free of a win as Cliffhangers. But the contestant said + without seeming to give it much thought. It seemed like an absolute guess. I think if they would have just asked her which is more expensive, Italy or Samoa she probably would have gotten it right. But instead she missed out on $30k worth of travel because of this sort of confusing game.
I'm not using this as an excuse for this person. Even if you had never seen the show and stop for a ten seconds to think this out you could probably figure it out and many people perfectly understand it, but I do think it is slightly confusing.