You must clearly define roles and responsibilities while addressing all the what-if scenarios.

Are lien waivers common in Indy?

Definitely the way to go on rental properties if you are an out of state investor NOT looking for an enormous undertaking with a BRRRR type scenario or investment of that nature or part time or full time job.

Zillow is very common but beware that a lot of these sights don't give you vital information and only give you a "Renter Score", not an exact credit score or other vital info.

This is a fairly common situation.On whether you should "let him go" or not, the question is, are you going to hold him to the terms of your lease regarding early termination or release him without further rent or early termination obligation. 

Anyone can model profitable scenarios but not everyone can execute.

I think it is common to analyze deals and see negative cash-flow, BUT what are you analyzing?

Lets discuss some bridge, fix and flip, ground up construction and DSCR loan scenarios for both purchase and refinance options .

I realize that turnkey properties mean you can’t improve equity so a re-assessment would not add lending dollars, but is there a scenario where the numbers work? 

Im torn between something that is turn key with encouraging rent potential v something old that needs a lot of work but can become 2 units, however not the best neighborhoods.Lastly, but very important-  If in either scenario price jumps to $380k with 15% down does this become not as profitable?