My plan is to build 2 smaller units (less than 1000 sq. ft. each), so designing ahead/purchasing plans online is feasible as the builds will be fairly simple - thanks for the tip. 

@Tony Cap, usually I would try to give a very pragmatic answer, but in your case the answer is pretty simple.

@Lawrence Paul Well the simple answer to this question is what does the math say?

It is time I look for my group of friends that can help me peruse what I want to do rather than explain to me “how it doesn’t work” or say “its not that simple”.

Its as simple as making a few calls and letting them know you would like to start your real estate journey today* Work or volunteer for any other kind of real estate company (ex.

Also, you could check out AirDNA which has great stats for short-term rentals.You do have to register with the city of Chicago, Airbnb makes it pretty simple but as @Brie Schmidt mentioned there are specific requirements to get approved. 

Hey All, does anyone have a quick, simple offer letter for cash investing purposes?

You could offer the cooperative siblings an amount in exchange for her signing a quitclaim deed -which is a simple one-page deed granting all of their interest in the property to you.

Post frame, or balloon framing, is a simple framing method that was common until the introduction of stick framing and increase in labor unions.

A complex thing can't be made simple.