I also don't do that long form where you ask for every bank account, credit card account, and previous landlord they have had since 1981.

Yep, we built our house of card up another level. 

Since then I’ve bought one duplex, I bought my own house and also applied for multiple credit cards (which were accepted) and a line of credit with my bank.

Another side note about finding roofers I didnt see in this post is go to your local lumber yard and theres a good chance they have a bulletin board with tons of small companies business cards that need work or just ask the people who work there.

Credit card How did you add value to the deal?

They could come in the form of business lines of credit, credit card stacking, short term & receivables based financing. 

The only thing I can pay off is a credit card which is a tiny $90 monthly payment.  

It's the slimy, dark underbelly and the best place to fence your stolen goods.

In general I love paying for materials that way I can negotiate solely on the labor - however, when doing this locally you have more opportunities to take the logistics out of the contractor's hands (for instance, how materials get to the site and making sure they aren't stolen). 

He will most likely need to file bankruptcy here in the near future (credit cards) while she is on Social Security Disability so her ability to support herself is very limited.