How much travelling will the different teams actually be doing, how far away - i.e. how expensive? Can you get a sense of whether they will be playing the same tournaments, or different ones? If he wants to be challenged, but will be playing in the lowest level tournaments, that will not be as good as if his team is in tournaments playing against better teams. Then you have to figure out whether the cost of travelling is worth the challenge and development differences.
I agree about the driving - I have great memories of that.