The method outlined by Doctorow in the linked article would not work, and here is why.
1) They (the government) consider not only the speech of disclosure, but the intent to disclose, and probably therefore the means of conveying the message that constitutes an act of disclosure. When an actual NSL is issued, I would bet the method described in this article could be regarded as an act of disclosure by way of clandestine communication. You would get in trouble for doing this if you were subject to a NSL gag order.
2) Doctorow's method is more particular than the Librarian's method. It actually does involve arrangement of a designee to receive information specifically related to government intel queries. It plainly establishes both intent and expressly indicates means to convey the state of intel inquiries to special parties. The DMS cannot be restrained from publishing anything, but those receiving the gag order conceivably could be prosecuted for communicating with the DMS service.
Finally, and most importantly, the agencies already note that disruption of electronic communication services (like account suspension, website shutdowns, and so on) can be regarded as signals to special parties that an investigation is under way. So, they (the NSA, FBI, whoever) forbid peculiar irregularities in habits of service when they issue nondisclosures. As far as Doctorow's method is concerned, you would likely be prohibited from failing to update your information to the dead-mans-switch in any way other than routine so as not to indicate you have been asked to provide intel information. See, you're providing a service to the DMS, disruption of which service might reveal a security investigation is underway: you can't do that, and they say so in their letters.
Look, I'm not writing about whether it is right or wrong for the NSA to do this, nor whether it is right or wrong for us to expose these situations. I'm just saying, it may seem like a cute little language game for solo citizens, but real companies can't afford to violate a NSL or any other gag order, and that's why they don't do it, plain and simple. The language of the law is pretty clear about why disclosure is prohibited, and violating that law looks to have some pretty severe consequences. Especially if the FBI or NSA or whoever is right when they say that disclosure is a threat to security, and then you're in a world of hurt because your unnecessary expression of speech actually did jeaopardize an investigation where intelligence of a credible threat was real. That's why currently it's up to the courts to remove a gag order, which they can do, if the NSL is BS. Your right to speech is intact; it just has to be reviewed and upheld before you can exercise it. Wait... that doesn't sound right...
However, while the article's method is dubious I think its underlying premise is worthy of further examination. You've tried to find a way to hide the fact of disclosure, or at least put it into legal safe zone. That won't work. Perhaps find a way to hide intent of disclosure?
