Pay close attention to guest feedback to understand what matters most to them, and highlight those features in your listing.

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

@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 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.

For my fix and flips I use the class designation (each property is it's own class).

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.

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

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". 

I use the state-specific lease feature on Avail.co.