I have never fined tenants based on the water clause and my guess is you never will either but I have used the government regulations clause multiple times."

I don't see any line of logic (or regulation on a national level) that would prevent this. 

@Bruce Lynn in another environment non-approved buyers might be fine, but in COVID people are trying to limit showings to only serious buyers.

I appreciate the input, but I'm not looking for advice on Jersey City AirBnB regulations, as I've done my hw there and it doesn't appear that they apply to this particular investment situation.

Are any Destin STR owners worried or thinking about selling due to the new regulations 

. : )  1 month is basically not short term rental, hence your ability to rent only to that since it would fall under a long term rental regulations most likely. 

We both know it will fail the inspection, because Trumbull county has strict regulations.

However, I'd like to get out of the corporate environment soon, but can continue with it longer if need be.

city county state regulators generally don't enforce deed restrictions.its up to the community were the restrictions are placed.. if its just one parcel with the restrictions.. you as declarant would have the right to defend thembut no one else if they are not subject to the same deed restrictions.it goes both ways.you look at CCRs from the turn of the century up until about the 50s  and there are all sorts of un enforceable things.having to do with Race religion  Chickens Pigs other live stock.. 

On charging a tenant, that is lawyer territory and would depend on your lease, the tenants willingness to sue, legal environment in your area, etc.