The loan is with you, not with your tenant, so none of that means anything to them - in fact because you live in one unit and it's under 4, if you were self-managing you don't even have to abide by fair housing laws (at least on the federal level). 

As a broker, you’ve already got a strong foundation, which will give you an edge in finding and structuring great deals.Since you're in Chicago, have you considered house hacking as a starting point?

House hacking a 2-4 unit property with FHA (3.5% down) or Conventional (5% down) can be a smart way to start, while DSCR loans or partnerships can help if you need alternative financing.

That journey started in 2016 when I bought a duplex to house hack.

What if I told you that you could purchase your house by only paying for 20% of the property value?

How much less will a potential buyer pay for the house, now that one "bedroom" does not have a closet?

Or 30-40% and they split the cleaning fee revenue with owners.

There is an affordable housing crisis here in America.

My preferred options are:1. house-hack with a duplex under ARV; live in one unit => renovate => rent the other unit2. buy a SFH under ARV that could be converted into a duplex (preferably adjacent units vs top/bottom) - I'm assuming the biggest challenge with this strategy would be separating the infrastructure for utilities; and costly.

We plan on living in the house and doing most of the fixes and renovations ourselves.