We designed it so no windows look into the main house.

The system is designed this way.For any tax benefit, for instance the STR loophole, you may qualify in one year, not qualify the next year, then qualify again the year after that.

@Jonathan Klemm thanks for the mention@Ali Farhat Jonathan is correct that you may still have some opportunity depending on the Zoning designation for the lot, and how many existing units are Legally Recognized by the City.You can Check the Zoning Designation here on the Chicago Zoning MapFrom there, you need to check the requirements for your lot based on the Chicago Zoning Ordinance (Note: RS-3 does not mean 3 Units.

I've been educating myself through books and podcasts on topics like sourcing off-market deals, deal and property analysis, creative financing, and title reviews.My fiancé is an architect that works with GC's and structural engineers to design homes ensuring they are functional, aesthetically pleasing, and safe- which I hope will help me navigate this space as I grow my knowledge.

@Nina PenuelaI feel courage, humility, and adaptability are some key characteristics.One must have the courage to act, to engage, and to challenge.

I received little to no response for months regarding various issues (apparently due to a software bug and there was no PERSON to call because the platform is designed to be tech savvy).

The reality that neither view is realistic or probable.The best advice I can give would be to underwrite for long-term leases as that can be an acceptable exit strategy, but be prepared to execute well on your MTR strategy (great interior design along with profesisonal photos and concierge servive). 

Mailers as a mono-action to lead creation is ridiculous, and this form of marketing has never been designed for such any more than a billboard is for getting "leads". 

BiggerPockets is full of resources designed to help you along your journey, whether you are just getting started or a seasoned investor.

We could sell that house by itself, but it would be sold under a land in common agreement and an HOA would need to be formed.I also confirmed with the Public Works department that a 2nd driveway can go in, with a septic designer that there's room for second septic tank, and with the public water company that they can tap into the main water line from one of the neighboring roads.I'm sure there are some more details that I would need to iron out that the code officer didn't bring up, but the high level answer I was looking for is that my town does allow selling off a second house under the LD 2003 legislation.