I am orginally from Elgin, but living down in Logan Square area of Chicago proper!

I don't think you are going to be able to get insurance for two separate living units in a single-family when they are both illegal and likely do not have the correct egress windows (basement) for fire safety which could subject you to huge liability if something happens to either party.

I was living in Kennedy Town for two months last December.

Hi Devin, Have you ever considered that instead of America needing smaller homes that are more affordable, that America needs more higher paying jobs so that people can live the actual American dream versus having to settle for less and less and less (Has George Carlin pointed out in his classic speech about this). 

Burlap on the wall, postage stamp rug for a large living room, hodgepodge of items around the house with no real theme.

I am seeing a crackdown on STRs not so much as a result of any hotel lobby, but as a result of regular citizens complaining to their elected officials that they don't like living next to a hotel.Can't really blame them.

You live in a $1,000,000 house and are able to secure a HELOC for $150,000. 

You'll need at least 125-150 doors to make a decent living, but you won't be able to afford much help. 

. - The ultimate house hack, live in the small ADU unit and rent out the two levels of the main house on AirBnb in San Francisco (I would have thought STRs are oversaturated in S.F. but it worked for them and they stay fully booked).

That's where I live.