Is there any concern that the local government would ever ban short term rentals altogether?

I suspect this would happen if various parties were given the ability to ask questions in nearly every application for what this thread touches on - and I have major concerns about integrity (and credibility) issues involved in putting yourself in a position to defend this position if ever challenged. 

NMLS Consumer Access is a fully searchable website that allows the public to view information concerning state-licensed companies, branches, and individuals licensed and registered through NMLS.

Given this is one of the rougher neighborhoods, I'm a bit concerned that the next set of renters might not be as good as this set of renters.

All of us have stable jobs and no other outstanding concerns.

It also makes it harder for other operators down the road--- not your main concern but we all impact each other.What about you and your wife live in the garage unit, and rent out the house for a lot more, at least until all this permitting is figured out.

I also have a 3 family that I'm trying to refinance with a DSCR and I am concerned with the cash flows its in Chicago, IL. 

While I have seen only good things said about PPR, one thing of concern is that even though they started  during the great recession they do not have a track record of weathering one.

I’m not so concerned with how to turn them on, it’s more what immediate issues may I encounter when doing so and how can I mitigate them.

And I generally require a sponsor that has full real estate cycle experience with little to no money lost, low leverage, high skin in the game and reasonable fees and promotes.However, other investors will look at these deals as bad/too boring for them because they are more aggressive and not concerned about the risks of default, refinance, interest rates changing etc.