Again, this is an attorney question, but if I were an attorney (and I'm not), I think I'd assert fraud in this case. 

As far as due diligence, not sure what that all would entail.

Just make sure the agent who gives you the quote knows what the structures actually entail. 

Thankfully, I don’t need that kind of money live on, as I have my day job, however I would like to accelerate the payoff on that expanded RE portfolio with the mindset that all mortgage debt payoff will entail my retirement.I would love to get your thoughts/critiques regarding my plan.

In terms of the questions, in order to ask the right questions and have certain expectations of the answers, you need to get educated on what syndication entails and how various asset classes behave. 

I educate them on what their request entails from me, they see the work I put in because I am extremely transparent, and they appreciate me and me them.

One of my main areas to work on is my ability to be assertive and push my contractor while still maintaining a positive relationship...

Contrary to your assertion, the only 'emotion' involved is the basic background detail on the matter in the first paragraph, another point in reference to the fact that we typically aren't coldly calculating and trigger happy with regard to our tenants' transgressions, plus a summary to the extent of the personality type we are dealing with and the various permutations that we might consequently have to deal with.

But I have more than my gut and anecdotes to back this assertion.

Are you assertive, or a pushover?