It's too large of an investment to get it wrong; you need bench strength.Real estate investing is a risk business.

She’s currently not paying rent, and while she has some health issues and no stable income, she’s been communicative and open to general talks, with a possible option to vacate through a cash-for-keys arrangement, though this might take around six weeks and some hard work.I plan to rehab the property and eventually rent it out, potentially to a Section 8 tenant.

They have the time frame and payment dates set but I’ll be sure to make sure things are going as planned.

I currently live in it as my primary residence but had plans to eventually rent it out and then cash out refi once I reach 20% equity in the property.

She runs a business out of the homes.

I am taking your advise, and switched my game plan to include a local agent or property manager to show the properties. 

It would seem that turning a real estate training program into a successful business is very difficult because most of them are not around any more. 

Assuming you don't plan on going back into any consumer debt again I like your plan versus barely getting by.

It is the cost of doing business.

I recall reading about it in CNBC...The quest for solid returns in our current market might feel daunting with interest rates where they are, but the good news is.. if you find the right deal and set clear criteria.. like a minimum cash flow target, or a plan for eventual refinancing.. your numbers can still work out.