I've seen some recent articles indicating that Booking.com is trying to compete more against Airbnb. Currently our primary source of bookings is Airbnb, followed by VRBO. Earlier this year, we were also posted on Book...

Then two years ago I decided to get my RE License.

A couple other neighborhoods I like besides the two you mentioned are Washington Park, Hyde Park, Woodlawn, and South Shore.I think that area will continue to be gentrified because you have the lakefront as well as CTA trains.Is there any reason you are targeting Chicago instead ofdoubling down in Kansas City?

Healthy tenant base and rental demand as well as two section 8 voucher providers in the city, CTI and LHA.

Given that your property has been subdivided into two rental units, it should indeed be compared to other multifamily properties in the area, not single-family homes.

I advertise the houses that way, even if there's an appliance or two that the previous owner has left in them and I don't mention them so that the people coming aren't (or shouldn't be) expecting to find them. 

Having two people paying rent, but only one living in the house is not ideal unless both understand clearly they are liable. 

It's not going well so now two of them will sell it to the 3rd.

The net result is basically the same, but it keeps the two properties separate from a lenders perspective.Any low down payment money, particularly on an investment property, is going to come from a private money lender.  

My two cents are with 400k,  pick a market and get started.