The second time, the case won’t be dismissed, because the Supreme Court isn’t dumb.
I was wrong. SCOTUS denied the motion April 29. Looks like the case will move forward.
Oral arguments are scheduled for Dec 2nd.
While the case has been set for argument the Court did not totally reject the possibility of declaring the whole thing moot.
Per Scotusblog, "[T]he justices made clear that the case will move forward: They rejected the city’s request to dismiss the case as moot immediately, instead announcing that the “question of mootness will be subject to further consideration, and the parties should be prepared to discuss it.”
This does mean that a certain part of the very limited time for oral arguments will likely be devoted the to question of mootness leaving less time to deal with the heart of the issue.