His health is heavily compromised, the local agencies are not helping him much(who he uses for medical, food or moving needs) & he has much trouble getting around.

The agents focusing most heavily on getting referrals are the ones that are succeeding in the long run.

As for buying real estate when your heavily in debt, I think it's unwise.

Your assembled portfolio will be heavily financed enabling you to buy more properties.6. 

The issue we are having is finding lenders who can close quickly and who won't lean on the income of our LLC based on the past couple of years' tax returns too heavily.

There I worked heavily with single family housing development (rental and for sale), down payment assistance program, acquisition/ rehab of abandoned properties, and overall community development.  

I even had my cashier’s check ready to purchase a sweet foreclosure at a heavily discounted price.

I am located in Raleigh, NC so the real estate market here is inflated heavily due to the volume of new movers (including myself).

In addition, expect fracking companies to default in record numbers in 2016, pulling heavily on the Cleveland market. 

If you have pictures, place an ad on Craigslist and Postlets listing the unit for the top end of the rent and see how much of a response you receive.Also, banking on a 20% increase in appreciation to get out of PMI is a risky bet so don't rely too heavily on this.