This is beneficial to me for him to stay and pay till that time noted due to the terms of my deal and I would be rehab and flip property after tenant is out of picture.

Husband and wife team here as well (wife not pictured, that is my dog). 

Investopedia is on the right track saying that the rule is supposed to ensure it covers your mortgage, but it's much more than just the mortgage, it's the insurance, taxes, maintenance, etc costs that are in addition to your mortgage.

Look at the market, if an investor or homeowner bought this, will they collect enough in rent to cover the expenses they have ?

Here on BP you can do that by adding a picture to your avatar.Understand that beyond understanding the technicalities of rules and regulations, real estate is about market conditions and helping people to get to yes.Get to know your target market like no one else.Develop your ability to empathize what's going through a buyers head and a sellers head and figure out what you as a real estate agent can do to address concerns.Neither of these are limited by your age.Good luck!

All local news outlets covered the opening, I did a mailing campaign, social media ads, etc.  

I have about ~40K equity in the rental and owe about $157K on the loan, but the monthly rental income only covers the mortgage payment + insurance + taxes + an additional $75 a month, which I put aside for repairs and anything that may come up.  

At the same time I will start the forclosure process to cover myself, and compel him to sell it. 

It's funny because the online course has actually covered this question in classes since I originally posted, so I was just thinking ahead I guess.  

You can get a commercial umbrella policy but that will not cover your own residence and autos just the commercial properties.