If the compounding increase in technology once gave the advantage to the settled, a line has been crossed. Now the advantage can go to those who are returning to the life for which humans were originally designed. That's not at all clear to me. He's also a nomad himself. Ogilvy may be right, but it's not easy being high-tech homeless.
Ordinary transactions become very complicated.
This is harder than it sounds. A key decision is which two nights you spend in the same place to get the washing done. One consultant views it as utterly unremarkable that he sometimes has his shirts sent to his next location by Federal Express. Many nomads have their bills routed to their accountants or lawyers. Electronic banking has helped.