I had a horrible experience like that in a New Orleans apartment complex, back when I was a renter. 

To make a long story short the renters where horrible and no one was taking full responsibility of paying the refi.

I never do that, but these people had good references and it was January which is a horrible month to rent here.Have you considered rather than charging double deposit to just charge the extra $75 per month?

A good example might be a property with rent potential of $800 but smells like cat pee and looks horrible. 

It's right next door to my apartment complex and it's in horrible shape in a run down rural neighborhood.

This is my brutal assessment of your horrible situation.You wrote:We have a family friend who has been a contractor for over 16 years, so we chose him to build our house.

They are uneducated on real estate, so their advice is usually horrible and works against you. 

I'm sorry to hear about this horrible and expensive learning experience, and I wish I could help.

I feel horrible about the roaches.

Ive have horrible experiences (bank took months between updates even though we have a law that says they have to respond within 30 days, because if you demand a response, guess what it will be.) it took 10 months to get a final agreed upon price.