What blew up my whole plan was learning that it can take 1.5 to 3 years to get plans approved by city planning department and local neighborhood approval committees.

I'm on the forms committee for NSBAR and the neighboring boards were notified by CAR that any agent that is not a member of CAR is strictly prohibited from using CAR forms.

What a great welcoming committee...

You state "following approval from zoning committee" - has that approval actually happened?

Someone on the zoning committee said they are restricted but there are a number of AirBnb's operating in the area right now and I can't find any info on applying for a rental permit. 

In this instance, it is a hyper local issue that is relevant to Cook County and to Chicago - there are 2 ordinances that have to be followed.Second, the examples I gave came specifically from the Fair Housing Laws for Chicago Housing Providers presentation given by Chicago Lawyers' Committee for Civil Rights (CLCCR).

There is no minimum number of days you have to live in your residence for it to be considered your primary residence.Now ... what I'm hearing at the city's Short Term Rental Advisory Committee is that they may change the ordinance this year to insert a minimum number of days you have to live there.

At this point if you look acceptable, at a portfolio lender, your loan officer will take your deal to a loan committee which will decide partly based on your deal, your risk and probably on what the bank already holds and wants to hold if they want to loan on your deal and at what rate.  

They don't have a Loan Committee for Christ's sake!

This would not pass scrutiny from regulators, auditors, or their loan oversight committee (unless some sort of "shady" institution).