On the whole, I think society probably benefits from this kind of edge testing. I certainly don't encourage it. And taking on federal or state laws is a different game (legal and moral liability-wise) from challenging municipal codes, particularly when people get hurt.
But Uber challenging the taxi industry forced everyone to take out the rulebook and reconsider what is and isn't truly necessary. Something similar is happening with hotels. One could argue, with Bitcoin et al, too.