I think it's going to be a lot harder to get yourself a TLD than people think. In addition to the large sum of money, you also have to prove that it isn't offensive and doesn't infringe on anyone's rights and "the business or organization must prove that they are either capable of managing the TLD or can reach a deal with a company that will" [from the ArsTechnica article]. These obviously won't be issues for the eBays and Amazons of the world, but how many squatters will actually be able to prove they can manage a TLD? I'm no expert, but there's gotta be some huge technical and maintenance issues there.

I'm also curious if people who register TLDs will be required to allow the general public to register domain names under them.