By your quote, it sounds like Centerville is passively against it and will only punish those who are bad landlords. 

However, traditional lenders will punish your DSCR and DTI once they see multiple properties in your name.

But things took a turn and the tenant started blasting music during the day to annoy/punish the upstairs neighbor, which turned into the other neighbor doing same, then cops getting involved 3x in one month...

Absolutely.If they did somehow find out, the punishment could just be that the lender calls your note due, in which case you would need to refinance to an investment property loan, or be forced to sell if you can't qualify for that.Or it could be worse, if they can prove that you intended to defraud them and not actually live there. 

If capital gains increases, 1031 goes away, property taxes go up etc - they all punish the owner/landlord.

Dept Public Health Laws <-- This is what I read and didn't see a "punishment" section.

If the seller is getting the BEST off possible from the listing agent who brought the best buyer and then negotiated the deal highest, it makes zero logical sense that agent should then be punished for that.

I did this once and called the appraiser roughly 3 weeks later and it was like a bombshell, he again said you bought it for so low I told him so your punishing me for a deal that I found and no one else?

Our lease waives the right to a Jury trial but the waiver might or might not be upheld because of unequal bargaining power of the parties but it's more likely to just be thrown out than to be financially punished by the court.

School doesn't teach you that, it just punishes you for making mistakes.