All I asked him was "How will you travel anywhere, when you'll need permission to cross thousands of individual jurisdictions?"
You're telling me that problem doesn't exist now? There exists 2 concepts that render your argument fallacious: self interest and pragmatism.
Imagine seeing a helicopter flying over your residence (one of thousands of "jurisdictions" as you put it) in a future Randian "nightmare": what sort of dickhead is going to get on the comms to said chopper, threatening missile attack if they don't pay the passage tithe? I suspect you would (quite reasonably) think: "Live and let live, one day, I may need to fly over this guy's house also". And maybe those dickheads will exist, but, guess what? Those dickheads exist now anyway, they're called military air traffic control.
At least in the supposed nightmare scenario, such a thing as safe zones would/could exist for aircraft or other transport. Right now, it's either pay the extortion fee, get killed by military aircraft, or spend your life confined to just the one tax farm with the rest of the cattle.