Something I did not mention in the original post was setting up a lease, my guess is that the best bet is to find a boiler plate for the state you reside and then consult with a lawyer to custom fit it to your needs?

Video walk through is your best bet.

I would put bets on it being one or more of the first three, versus the fourth. 

Now that I'm more experienced and cashflow is less important, I may take a deal that has zero cashflow and bet more on appreciation, but only after accounting for all expenses, including setting aside money for capex or vacancy.Here's a guide that describes what good cash flow looks like and how to analyze a property.https://www.biggerpockets.com/...

I just know it's a safe bet with growing population, good taxes, good schools, fair laws.

This will likely kill your velocity to scale.It sounds like a heloc on the townhouse and then conventional at 20% without the occupancy requirement is your best bet at keeping and maintaining velocity.

If you can wait, that's your best bet. 

Adding on the fact that similar properties closer to Nashville tend to go off the market really fast, this ashland City property seems like my best bet for just getting started. 

Considering she has excellent credit, strong payment history, and assuming low DTI, I would say there is a strong chance she gets approved.As Malcomb said, your best bet is going to be calling some lenders and talking them through the scenario.Good luck!

There are three cups and you bet say $20 that you will be able to follow their hands to decide which cup has the ball underneath.