In addition, there are a few main components of the structure to consider: exemption status (506b vs 506c), equity split, preferred return, fees and waterfall hurdles.

I am trying to determine if I am being unreasonable or to impatient and looking for advice. 

The first hurdle with that would be finding someone willing to loan you the down payment and rehab costs when you have no skin in the game and they'd have to be in second position behind the conventional loan. 

I am tempted to be ruthless and request the late checkout amount in the Airbnb contract (2x the nightly stay), but it admittedly seems a little unreasonable.

I would fear that if performance hurdles aren’t hit in a big way, sponsors lose interest, and then they take their eye off the ball.

You're being completely unreasonable and I would probably do the same thing your tenant is doing.

Unless we can acquire all of our financings from PMLs, I imagine that financing will be our biggest hurdle. 

Many of the hurdles you experience in real estate (and life) will be self-imposed and are much easier removed that you may think.

My biggest hurdle in all this will be the infamous analysis paralysis but I'm hoping at least my awareness of my proclivity toward overanalyzing will help me avoid it. 

They do not take the time to know what a tenants needs really are let alone how to handle a tenant that might be overly needy or unreasonably demanding.Accounting — I have to audit the statements on a regular basis.