This won't work for the simple fact Tom claims (in effect) that we can't know the true distance between any two points unless we've personally walked the distance with a measure of some kind. That's why he said we don't know the distance from New York to Paris.
Yeah, I got that. My proposed method is:
1. Find any reasonable distances between the four places used in the proof that would work for a Flat Earth.
2. Then calculate the speed at which planes would have to go to travel those distances and be on schedule.
3. See which ones are way too fast, which ones are way too slow and adjust your distances - again so that a FE is possible.
4. Repeat 2 and 3 multiple times.
I think that at some point, we will have reached some kind of equilibrium, where the values for the distances are as accurate as they can get, assuming the cities they connect are located on a Flat Earth. If the times, velocities and distances match up, then we have proof that a Flat Earth is possible. If they don't, we'll have proof it isn't.
I hope I was able to formulate it a bit better this time
EDIT: Could someone please just tell me real quick if it will work? I really want to go to sleep right now, it's 3:06 AM