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

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.

A simple DSCR (rent/PITIA) calculation can be an easy way to evaluate the property if you are doing that type of loan.

@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.

Make it simple on yourself.

We have a very simple proprietary profit/cost calculator for fix and flips.

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). 

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

Secondly, the more time passed by, and the more I've seen, the more HORROR I observed the program caused to simple people. 

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