What I call "pizza box syndrome," where they'll eat most of a delivery pizza and forget the rest to rot in the box in a bedroom corner.

They are currently rented with window units/space heaters. 

@Mike Balcom,Forget that he is a handyman-- structure your 'partnership' as you would any other. 

I have never taken a drug test for getting a loan :). 

And I am aware the max you can build is 1100sqft, and I have done all the background work to make sure I have the zoning, meet all the FAR requirements, impervious cover, etc.Any recommendations on the project in generalFor anyone who's done a project like this:What is the timeline I should expect for getting all of the necessary permits before we're even able to start construction?

What is everyone paying for your standard Low E window installed in the Raleigh Durham area?

I must still be confused...so...lets go off example 1, forget my example 2 it wasn't a good one.Purchase Price: 156k... 20% of that for a down payment is $31,200.   

However, my family member saw that the neighborhood was starting to head in the wrong direction when they saw that some windows were being boarded up down the road and people were letting their lawn and shrubs wither.

Then, look for distressed properties - ex. poor landscaping/tall grass, doors off hinges, broken screens and windows, etc. 

She's a good tenant, just flighty and forgetful sometimes it seems.Thanks!!