If I do this, my intention is that things are smooth and drama free for both sides - but of course I need to know that if something goes sideways my "First Position" isn't just a security blanket phrase...but rather, something enforceable and real.

(I know you didn't start the phrase but I see it bandied about in this thread.)  

If one landlord shows for 10 years CHECK OUT THE LANDLORD.Key phrases to listen for."

He mocks "some guy from Utah," a successful RE investor who also teaches a 3-day course, without telling you that he took the course himself and teaches much of the same material and uses some of the same cute phrases, e.g.

I have a duplex unit up for rent right now and have a phrase in the description saying "Not set up for Section 8".

The " the home is not approved for the Section 8 program" phrase was specifically mentioned in the course as not being ok. 

Most of them were the friends/family that I should never have rented to though.Even the fact that its on your application will dissuade some would be poor tenants.I don't think it's that hard to figure out it they gave you a real landlord or a friend if you phrase your questions correctly.

When you use the phrase "cashflowing" for the rest of your properties do you use it in the same sense (just revenue - PITI)?

You are right, I didn’t phrase my question correctly.

Getting one's ducks in a row and laying out all the information for Buyers is part of a Seller's sunk cost of time and is going to happen regardless at some point.You can phrase it nicer to him, of course, but the bottom line is he's going to have to provide the info at some point.