I would visit https://syndicationattorneys.com/ for all the info you'll need on legal.

I would contact the housing authority who manages the S8 program in your area to get an accurate ideal of how they determine what they'll pay on the tenant's behalf.

I sent you a DM to gather some more info on your scenario. 

The issue it seems, is too much info, too readily available.

Contact local lenders, mortgage brokers, or even credit unions to understand the current rates and what your approval chances look like.

Many of the suggestions (and contacts) that were made in this thread have made all the difference.

Quote from @John Mason: Anyway this is an example of a search for HELOC  I am sure you can find many many morehttps://www.biggerpockets.com/forums/853/topics/1088137-helo...This is great info. 

I would go online and check other rentals in your area to see what other management companies are out there, and start contacting them.

If I were you, I would be firm with needing rent more timely, I would still contact the male because she can't kick him off the lease, and I would have a conversation with her along the lines of "this is clearly not what either of us signed up for, is clearly not working, and what can we do to get you to a lower cost living situation as soon as possible?" 

Contact a real estate attorney and let him put the paperwork together. 2.