That's just it, though - the inventory is so depleted there's no way the higher prices make up for the lack of inventory.

Then, you could make improvements, clean up homes, bump rents etc as it is near certain that this unfortunate gentleman has neglected things for a while.

Costs for rentals can quickly deplete any CF you have and the less dollars per door, the more risk you assume.

If things go bad, you could end up needing a lot of cash to clean up the loose ends. 

As for the house as it stands:$51k owed on mortgage2% interest rate, adjustable till 2018Houses go for $100k in the neighborhoodHamp incentive($1k applied to principal per year, payments made on time)$12k lien(credit card debt)biohazard clean up, cost ?

Had I not bought in cash I would be in a negative cash flow position after a tenant turnover which required more maintenance and repair/cleanup than anticipated.

The clean up costs were 2/3rds of the budget for the entire job . ( I felt sorry for the guy )  The addition was never built .The one thing you forgot , a good contractor will properly vett a customer and also ask for a drivers licence , check to make sure he is the legal owner of the property , check for judgements and liens , and how many lawsuits the customer has been involved in . 

When people ask us, we tell them that allow well-behaved dogs for a $25 pet fee and state that they respect he following house rules:Tenant needs to clean up after it in the yard No animals on the furnitureNo Wet/Muddy Dogs in the houseThen we provide a little doggy basket with a towel + lint roller.

I am looking to hire someone to do bi-weekly cleanup, grass cutting, basic yard maintenance on a property in Boston/Dorchester MA. 

The fees that you would pay on the policy greatly deplete your returns.