The thing is to sell conventionally - potential buyers understandably would complain about the Ticky-Tacky stuff.  

You will need to know all the minute facts about real estate transactions to avoid litigation.Buyers or sellers may rely on your advice and guidance, but there is a potential for lawsuits if you make an error or omission like delaying or canceling a sale or failure to disclose a material fact.

@Dillon Vansickle, first I would go to the listing broker and others, potentially from surrounding markets, to give you an idea.Second, most sellers are crazy today in their valuations.  

Hi BP,A deal that I'm currently working on has the potential of involving 2 separate partners, not including myself.

No I'm saying for the attorney writing the opinion letter there is the same work and potential liability. 

Landlord provides tenant (at tenant's decision) the option to limit potential damages by agreeing to pay 2X rent as lease break fee".

My best advice for getting started is to learn to run your numbers thoroughly and then practice on potential properties that you see listed. 

Potential upsides and downsides?

I'm in the process of researching the Lafayette, Indiana market for potential rental property investments.

Even longer answer: talk to an experienced accountant about potentially treating your lending as a business and structuring it along the lines of what you suggested.