Price still seems a bit too favorable and makes me think something is up with the property, like an assessment or major repair needed.  

Look up the property on your county's website (not sure but looks like this could be yours http://www.somervillema.gov/departments/finance/assessing).  

Seller further warrants that should the property be located in a Homeowners Association or Condominium Association that all past due assessments and or special assessments shall be brought current and evidenced via a Paid in Full Assessment Letter prior to closing.

Someone on your team should be assessing the problem, not the tenants.  

Keep us posted on the progress.  

Good luck and update us on your progress. :)

You can put in several zips and then narrow down by owner type (absentee, owner occupied) and many other factors (% equity, Total Assessed Value of the property, etc.).  

So you can use the income from you last return and show that you've been in business for 2 years ( maybe a business license that is at least two years old ) so keep me posted on your progress and I wish you luck. 

At the end of the week I assess the work completed and give him a draw accordingly.

While I sympathize with the situation, I also know that there is a fine line between gentrification and progress.