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.

@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.

The entire system is designed to just be this 1 thing, color int he lines, don't venture out, just follow these steps. 

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". 

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). 

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.

So I'll tell you now in case there's still time to do something about it:The problem I still have, that I can't solve (but maybe you still have time), has to do with the HVAC system.When you have a single house, and you're renting out the basement, you are asking the house to do what it is typically not designed to do in terms of the HVAC:  1.

Here in the Pacific Northwest any exterior (stairs) wood  rots quickly, so I choose to put my stairways inside.  1000sf for cars, 1000 sf on top, three rooms and full bath.

If it's just exterior, it shouldn't be a crazy amount of money.