I would expect buy-to-lease strategy is suitable strategy for people without "hardcore" backgrounds in interconnection, permit application, system design and project management.

It's very thoughtfully designed specifically for real estate investors by real estate investors so it doesn't have features you don't need and won't use.

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.

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

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).

@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.

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.