If your employer's payroll software is not designed to compute withholding amounts for more than 10 allowances, it will probably just withhold for 10 even if you claimed more allowances. 

I just switched my current company to an S-Corp and put my self on the payroll since I know lenders dislike us "self-employed" folks. 

Depending on how sophisticated the problem tenants are, especially in a state like New York that is very tenant friendly, you might be battling them to leave for months on end.

I have done deals like this with similar returns so I am not thinking it can't happen.. but I would consider myself a sophisticated investor and would not be asking people on the internet if it was a good deal..

If this is the case, then your LLC income and expenses are typically reported on your personal tax return, Schedule C (1040), under the same LLC EIN that you use for your payroll tax remittances.  

Or is it the opposite and they are heading off to find a less sophisticated investing group?

You'll use Life Insurance as the mechanism to replace the wealth you gave away, just as you would in a CRT.This is a 10,000 foot overview of three very sophisticated strategies. 

Don't ask me how it works, but it sounds pretty sophisticated.

Trying to come up with a sophisticated menu of options considering we are cash strapped and can only pitch in about 20-30% of the total cost.

Trying to come up with a sophisticated menu of options considering we are cash strapped and can only pitch in about 20-30% of the total cost.