What is the point of his behavior? If I was a jurist and an action was brought against him with that 69 page PDF file as evidence, I would rule against him as I would believe there was something less than legitimate in his activities/motivation. Just my 2 cents worth.
Wouldn't the law of diminishing returns kick in? If you spend $10,000 registering a bunch of domain names, then all you have to do is sell one of them for $11,000 and you've made a profit that year. But if you spend $750,000, you're anticipating someone somewhere paying you the better part of $1M or you've lost money on the venture. That seems a bit risky unless you're Bill Gates and the whole thing is just pocket change for you--which, in turn, changes it from a business back to a hobby.