I want to live here, its very peaceful and it has most- if not all amenities of a large city...I love this place...".

@Sean Wilt  The answer to your question, it is high dependent on the city rules regarding STR's.

I am looking for a general contractor that has done work in the Gloucester City area. 

What types of things have you folks seen from cities/government entities that have been helpful for investors while creating affordable housing?

The owner also shared that this is an "illegal" duplex but has never had an issue with the city, even when enforcing an eviction.Thanks for any advice on this one!

I know school districts are a big indicator and have also read about looking at the city planning website for future developments...but not sure what to look for specifically. 

It's important to have an agent or boots on the ground assistance to help you stay away from bad parts of the city.

DFW Mid Cities REIA - Great free group. 

In order to get approved for the rent amount you are asking for two things need to be true.  1) The rent you are asking for needs to be “reasonible” when compared to like kind property in the same city, within a 5 mile radius.

We get lots of city folk who do not know how to manage (or respect) the heat, fireplaces, firepits, cell phones not working, departure times, etc.