So, I am not sure how I would pursue damages and unpaid (2 months rent) if I wanted to.In hind site I should have kicked them out, but I didn't - lesson learnt.  

Very certain we overpaid, but it was a dire situation where the old one broke and had caused water damage and the tenant didn't notice for a month... 

A DSCR is a debt service coverage ratio loan (against the new property) and effectively uses a proportion of the current or proposed rental income to qualify.

I heard some believe no local agent that knows what they are doing would  sign this and on the other hand some are very skeptical the city would even  enforce this given the domino effect it may create. since I am considering buying a new investment property in Cleveland I  would like  to know: are there any solution if the city decide to enforce this?

I don't really want to, but the rents in the area are pretty low, and its not cost effective for me at this point.

You are going to want to file a claim against Person B and hold Person B accountable for the damage.

While this isn't common, I have know people that bought their first rental and when tenant moved out, had caused close to $20k in damages and skipped town after one year of living in place.  

I offered a reply asking about damage to gutter.

We use Bizcor but likely I think they are for larger portfolio sizes and may not be cost effective for just one unit.Having a direct booking site is a great idea. 

Hi Dustin,     In my opinion, based on your big picture goal, It may be more effective to hold onto it until you meet the bank's eligibility criteria and then sell it while the market is still extremely hot with very low inventory (especially in Worcester!)