Then I factor in the side issues that can impact any of the parts of the equation - the neighborhood for appreciation & ability to rent factors; known capital expense issues, or those known to be upcoming; interest rates; unusual maintenance needs (example: I strongly avoid homes without eaves); local property tax and insurance anomalies; ETC.In your example I would run from that house like I would from a grizzly.

@Stephanie Goodman, this is MA, and 20K Cash for Keys is not unusual, especially with a previous foreclosed owner as the occupant.  

Due to their very short-term nature, bridge loan providers can be more flexible with terms for people in unusual situations.

Like low or no security deposit, but that would be highly unusual for a house/multi type of rental.

This summer it was not that unusual to see 25+ offers on well-positioned homes.  

That's pretty unusual but you do sometimes find those great communities that keep their costs down.

In addition, second interviews are often with different people, so it is not necessarily unusual to repeat some of the same information you have already given. 

That would be unusual.  

The entire electrical system had also been recently (& very professionally) upgraded to 200 amp, complete with a new NG Generator.The exposed ceilings in the upper floors showed sold steel angled reinforcing of the rafters given the unusual flat roof configuration & our snow loads.

Unless there is something unusual about the property it should be worth the potential cash flow divided by an appropriate discount rate for the area.