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The number thing is abusable. Witness facebook still operating under the SEC's 500-person limit:

http://dealbook.nytimes.com/2011/01/03/facebook-and-the-500-...

I'm not aware of any measurement method that any moderately smart rules lawyer (aka anyone who's played more than 5 hours of a strategy video game or pen and paper RPG) couldn't figure out a way around.

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One way to frame that is "This is abusable. All you risk is the NYT writing an article trashing your behavior." The 500-shareholder rule is fairly obscure among laypeople, and pretty much only popular among people who litigate the cases it creates. So someone patent-trolling might suffer even more.

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