The bar is much lower than whether or not the court thinks the speech is protected or not. The court could unambiguously believe the rule is unconstitutional and the speech was protected, but if they believe there's any room at all for 'reasonable disagreement' on the matter among other judges, then the officers and officials get immunized.
> The municipal liability is just much clearer.
This would be nice, assuming courts agree, but until officers and officials start getting held personally liable for these events, they will never stop happening. If the PD and officials are shielded from liability but the municipality isn't, then all that happens is that taxpayers will continue to pick up the tab for police misconduct.
> In this case, the town's law is itself being challenged. Again, much clearer.
Well, he's seeking damages from the mayor, officers, and municipality first and foremost; the council rule has actually already been removed. I hope you're right that he might get something from the municipality, but I doubt he'll get anything from the mayor or PD.