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... ...spend your life confined to just the one tax farm with the rest of the cattle.
Point taken. Either way it's a problem, but I wouldn't be in favor of creating even more overlapping jurisdictions, boundaries, borders, checkpoints, and toll booths, which is what this hypothetical hyper-privatized world would likely devolve into...
Personally I don't see that much difference between the Randian utopian society and the current system. Sure, taxes suck, it's hard to run a business due to excessive regulation, and the elite hold all of the cards. Remember that Alan Greenspan, Mark Cuban, Travis Kalanick, Peter Thiel, etc. are all Randians. These are some of the biggest douchebags on the planet, tremendously powerful and rich, and hugely influential on US policy.
The only place the Randos shine is their foreign policy IMHO. Ron Paul is alone in speaking the truth there.