Since you mentioned that you are getting started, I highly suggest you house-hack (this is how I got started in Costa Mesa, Orange County).

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

There may be a couple of houses on the block that do not have driveways so this may not be the only one.

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

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.

Some are looking for longer term housing and need a place to stay in the meantime.

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

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?

We have a house in an opportunity zone in Texas that we bought in 2015, lived in for 3 years, and then made a rental in 2018.   

We're having to reorient our entire portfolio and sell pretty much all our big houses and condos because they don't cash flow anymore.