I'm all in favor or changing laws - but here the case is more difficult than a law that obviously has been overtaken by reality:
* One issue here is widespread tax evasion. There's no way we can have a debate about tax evasion by just stating "that law should be changed, I'm not paying those taxes." And AirBnB was clearly aware of that issue, yet they chose not to do anything about it. Their FAQ even state that you have to comply with local rules and restrictions and now those that didn't have a problem.
* It's not like AirBnB is having this problem only in New York or in the USA - the same debate has sprung up in Paris, Munich, Hamburg and Berlin, indicating that the problem is more widespread and not a problem with common law.
* Registering as some kind of "I'm renting out rooms to short-term visitors" might or might not be a good thing for society. It certainly ties in with the above point - anyone registered would have to pay. However, this is a city regulation, it's not part of the common law system. The city could change the regulation if the majority deemed it appropriate though. Until then, this is not "opt-out" without consequences. You can either comply or bear the consequences if you want to challenge the law in court. Otherwise I could just argue that any regulation is not in the best interest for society and opt out. I, as an individual don't get to make that decision.
> The reason for this is that the cost to those being prosecuted is so high it constitutes a punishment in and of itself.
But that's not the issue at stake here. This is certainly a massive problem of the american law enforcement. I don't know how to solve that though, but that issue is reaching much further than AirBnBs feud with the New York GA. See patent trolls etc. that all leverage that property of the system to their interest.
> I believe it is one of the great political and legal challenges of our time to reverse this trend, perhaps you think otherwise.
I totally agree here, but I don't think that "ignoring any law I personally deem unjust or senseless" is the way to go.