Ok those two questions will help me understand my total cost and my monthly revenue. 

I don't have answers for all your questions but my opinion will be as long as you disclose to the sellers and they understand that they are selling their asset in a deep discount ( in your case $18500 vs $60K value) you are fine. 

So I kinda understand your frustration, but more details would be helpful I think.

She's finishing mfa, relocating and no job yet, but solid prior work history.

I want to enter Originations with more experience and a solid book of business with guaranteed deals.

I'm not sure I completely understand. 

I had a call with Skyler about Brent's TTP program today to get an understanding of what the benefits of this are vs.

I understand Zillow gives estimates and is not always accurate, however,  I've confirmed numbers through the county Appraiser website.

I had been of the understanding that a Settlement statement is a mandatory document at closing.

You are absolutely correct about the importance of understand which townships allow STR's, and also knowing the HOA restrictions for specific areas as well.