Funny you mentioned a $600K house doesn’t pencil out as a rental.

I see that you recommend NOT having my mom deed the house over to me in order to borrow against it.

However- as the land around them develops, the house will become worth less on the retail side, but at some point, a developer will come in and pay way more than the retail value in order to include their parcel in a larger development.

Working with the city to find a solution.There is a similar situation near me where an investor bought a short term rental house, rehabbed it, ran it for a while, and then got in trouble with the town after a neighbor complained and the town said short term rentals weren't allowed in the community. 

If the house is older than 15 years old and an ADU is added, it can become rent controlled.

Find Brandon's videos on YouTube for the "four square" method of analyzing homes and practice.

I can't give a tutorial re how to originate a note today, selling a house with financing in just one post. 

If you are just getting started here in Chicago, house hacking is the ideal situation.

To set the stage, I'm owner of a short-term rental property in the Poconos in PA and we use a property management company for bookings, maintenance/cleaning, guest management, etc.This past weekend we had a guest booking but when the guests arrived Friday evening the house had no running water, though it had been running fine earlier in the day when the Property manager (PM) was at the house to give a final check and leave the welcome packet.

I used my house hacking here in Los Angeles and utilized the equity to buy out of state.