More often, I see people in Chicago using the MTR strategy to side step the STR regulations.I've considered buying a SFH with an in-law arrangement in Chicago to use as an STR because to me that seems like the best way to employ the strategy.

If all parties were agreeable (and would likely agree on an interest rate lower than a bank's would be), with $0 down his monthly payment would jump $300-$500, but now he would be building equity in the property.Is there anything else I should tell him or anything I am missing?

Also, keep in mind that some aldermen have opted their wards out of AirBnB and the like as a blanket ban.

If it continues to perform this well we don't see the need to hire an appointment setter... saves a ton of headache as the position is definitely high turnover.Do y'all think a mortgage brokerage, hard money lender, or wholesaling company could benefit from a system like this?

And after checking out a few posts here, it looks like these zip codes may not be that great.

I would like to find a lender that would base financing on rent/income.To answer your question, the property is fully occupied. 

I can also point you to a ton of resources if you'd like to do your own research.

Since each of your LLCs owns 50% of the holding company, but the holding company doesn’t own your individual LLCs, the IRS will likely treat your LLCs as separate, single-member LLCs for tax purposes.

Any thoughts on a transaction like that?

I feel like my best route to getting started is by working with partners or private lenders given my current available capital.