@Andrew Slezak I recommend you first articulate precisely the liability events or concern which are pushing you to transfer the property to an LLC.

Most who are chasing doors have in their mind a precise amount of cash flow they anticipate generating per unit and believe acquiring a set number of units will help them achieve financial freedom, the ability to leave their W2, perhaps allow their spouse to leave their W2 etc.

What are the biggest headaches in moving toward a more precise billing model?

It's a fine dance that requires precision and response because as you know, it can be better to take a lower rent if it means not losing months in vacancy which can be more costly over the course of a lease term. 

Now the numbers may not necessarily be this precise, but it’s about “time”.

B. ) I'd like to know to know precisely how syndication works.

This is more precise in my opnion than trying to pin down specific monthly costs/revenue for each season. 

That’s precisely why the strategy doesn’t focus on “hiding” the dirt.

You play the risk game based off what you're paying & location.If you're really talking dollar for dollar, but not everyone can optimize so precisely.  

Your points are precise, and show an obvious disregard for the investors by the sponsor.