Basically, you get punished by the credit bureaus, if you make a payment on an old debt. 

To me, it punishes tenants who's hardly at home.

Am I punishing this seller for running his business smoothly? 

And the common denominator here and for your problems in Detroit is..... tenant selection by.... a PM.Why do you keep punishing yourself? 

Women get "punished" for not being "nice" in ways that men never do.Think about this if you have a daughter.

I need some one who I can trust that will come to work and do a good job... which makes me think, if the contractor builds something and the inspector say's its wrong... does the contractor get monetarily punished ?

"Blocking formerly incarcerated people from accessing stable housing is an extrajudicial punishment not consistent with the rule of law."

If the tenants are on an 18 month lease, you run your analysis using current rents as projected income. this lowers your purchase offer, and punishes the irresponsible landlord for offering an 18 month lease at below market rents when he planned on selling. if the lowest price he is willing to accept is calculated using market rents, then you compare your risk aversion and capability to carry the property at a loss for 18 months to determine if it is worth buying still. likely not depending on how far under market rents are.

I just hope that the tenant can get some sort of fine or punishment for this.

I could claim I overpaid at $800k and I shouldn't be punished tax-wise for overpaying but I have no numbers to back up a claim that the house should be assessed lower than $800k.