The proliferation of extensions is also annoying: I don't like remembering that "abc.net" is completely different than "abc.com". I think it would make (slightly) more sense if acquiring "abc.<anything>" at least meant you couldn't ever register "abc.<anything-else>", as then the only purpose of the extension is to identify who manages your domain.

Personally, if I see an organization with a "special" new TLD, I won't be impressed. I'll only consider them foolish for dropping half a million bucks, and assume that they mismanage their money in other ways (i.e. bad investment, steer clear).