That's so awesome to hear about your flips while stationed over here, very inspiring.

When you have been on that treadmill a while, it's hard sometimes to see that the only winners in life are those who are genuinely happy in what they do everyday. 

As my husband and I learn different topics on this forum, books and youtube, we get inspired/excited and have a rough draft business plan as we keep modifying it. 

(I will also mention that if you think it was genuinely set up a as a 2F in the past, there is a loophole for documented used prior to the zoning ordinance being adopted, but you would have to go back in the census archives from the early 1900s, and it doesn’t sound like this property really meets that description.)So I still think you should definitely ask in person, but I want to set your expectations that while the bigger lot is good (and would be a point strongly in your favor if this property was in R-2 or higher), I think the fact that it’s an R-1 zone makes this one an uphill battle to convert to a two-family.

You not only need to sell their house, you need to sell yourself and be genuine when doing it. 

You're a great inspiration!

As a compromise--because people in Chicago do love & appreciate some old world charm--we have gone with design fixtures and finishes that are modern/deco inspired.

This was the most inspiring and motivating thing for me because although I didn't actually catch all of the things people were talking about, I was able to feel the passion and excitement in the conversations.

I genuinely believe he didn't know and from his explanation he was confusing sales tax vs. income tax.

Yes, PMC's make money on the program, but not as much as you may think.Owners benefit directly from the mandatory Renters Insurance, and indirectly from the rent payments being reported to credit bureaus and the tenant retention gift cards inspire.