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. 

I would plan to long-term rent the property from day one and would never reside in the property before renting.  

It is the cost of doing business.

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

Their debts have either been wiped away or dealt with through a payment plan.

I use the terms -  "corporate furnished rentals",  "short-term rentals",  and talk about my target clients-  Business travelers, traveling nurses, traveling healthcare workers.#6  Knowledge -  Know why STR is better for the landlord than traditional rentals.   

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.

Thanks Ryan, now that I’m out of my busy season for work I would def love to attend.

i tell them all the time to find a good W2 job you like and you plan on staying with a long time. 

Selling now could simplify estate planning and lock in gains, especially with capital gains taxes in mind.