You asked for something that can give you high level numbers to which you could see if a deeper analysis is warranted right? 

Likely hood is that they would not move out they would stay and proceed with repairs.If the damage is serious enough to warrant your tenants having to move out talk to your insurance agent first.Get the place fixed and do not rush into a decision. 

For example, in your case Anthony - do you think your track record as a reliable borrower/mortgage holder gave your lender the extra reassurance to warrant that flexibility in the ratios? 

The homeowner just had financing fall through because this unit is classified by Fannie Mae as "Non-Warrant-able".

If you jack up the rent, you will likely lose those long-term tenants, and my guess is you'd need to put a lot more than $10k into this property in order to warrant a higher rent.

From legal standpoint, You may warrant LLC to begin with.Analyze you risk tolerance, your life outside RE, your insurance profile , and talk to the attorney to see if you need LLC from legal standpoint.

The condo will not be warrantable so there will be many fees involved.

It may not be the best option for you but I believe it warrants some investigation.Good luck

They know if you call the cops and report them they'll have cops with a search warrant knocking on the door. 

Depending on your circumstances, there may be a trade-off here - between payroll tax strategy (S-corp) and income tax strategy (401k) - which warrants close analysis.