FYI I'm an investor & a realtor, and I think it's off-putting to the other party if you try to negotiate again once that window has closed - it's just odd, unless there's something substantial and new that you learnt while in underwriting... but that's why you have the due diligence period etc. 

Having said that, your odds are better if you target a specific type of buyer. 

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.

That's odd.

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. 

For me, I am projecting 99 years old but I'm a little odd!

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.  

If you told me you were going to live there for the next 5 years, then that's a safer bet in my opinion.Another thing you may want to consider is to turn the other unit into a short term or mid term rental to increase the income and decrease your living expenses.