I live in a town with restrictions on STR's, but I purchased a multi-family in R4 zoning, because I saw it coming.

Also, completely agree on doing renovations ahead of time because living in a construction zone is no fun especially if you have kids! 

How was the planning and zoning board ?

You can get your GC license but I believe that doing so will raise some red flags with the FHA.

Too many red flags for my liking.  

The zoning only allows for single family.

Look at your local zoning and whether it would permit 3 units on 1 lot. 

There is more to South Philadelphia then just Point Breeze and each neighborhood has it good and bads to it depending on what you are trying to accomplish.Would highly suggest attending some RCO or CDC neighborhood events as well as there zoning meetings to get a grasp of where the development is going and does it fit your wheel house.

$140k with $1485 in rent seems pretty solid to me as long as its not in a war zone.

You have red dots for houses for sale.