I would look at non-profits and start calling newspapers and others as the court system will most likely fail you - a social media / online campaign against him could be the way to go AND you would want him to file suit against you - because if he did something wrong you have opportunity for discovery and he would have to open his books etc. and that is where if he was doing something wrong it would be able to come out. 

He has identified this helps him legally when going to court seeking Use and Occpancy fees. does this type of strategy work in other states?

You'll typically get a hearing where you can present your case.Superior Court AppealThe final level is appealing to Superior Court within 30 days of the Board of Equalization's decision.

"Could tenant try retaliation/discrimination claim"Absolutely, people can sue for anything and tie you up in court for no reason.

have not tracked court house in a few years  when activity was low usually meant opening bids were just to high..  

And you cannot have a STR where the property has been determined by the Chief of Police as being within the top 10% of properties with crime or disorder problems within the Town.Permit: No license or permit currently.HOAs: Good chance at finding non HOA here (still check for restrictions put on by the developer!).

Is small claims court the only option, or is there another path I should look into?

So now the debtor has submitted a plan that’s acceptable to the court.  

In NY, each tenant gets a pro bono attorney in landlord court. 

So we moved on to court, which had a 2.5-month wait.