I was imagining responsible car-free tenants, as I was one myself for a long time. 

Prices a few years ago were based on expectations of (in addition to interest rates staying low): - Then current operating cost assumptions (like insurance cost expectations being flat)- A seeming disregard for record levels of new inventory / supply hitting the market- Extremely high inbound migration expectations which are likely to not be met, due to both natural disasters and the boomerang effect when people from California or the Northeast move to the American South and hate every minute of the humidity, the large and relentless swarm of insects, and the occasional hurricane. 

--> Passive income doesnt mean tax free income.

I would make sure financially you have a good base and then connect with a local agent

If not, then what he is trying to do is to avoid his reputation going down the drain and lose any future credibility and trust in the future. personally I am just familiar with the basics of buyer seller representations in a general sense you will need a FLA Broker or Attorney to describe to you based on the documents you have if there is a Duty from the agent on this transaction..

House hacking in Chicago can be a game-changer—letting you live for free (or close to it) while building wealth through real estate.

Feel free to ask me any questions—I’m happy to help!

There are too many factors to consider to just provide base rates for what you're asking. 

It looks like you are doing an affordable build based on the cost but hard to say since you didnt provide info on the build itself such as square footage and finishes.

This motel has been great for the last 4 years, constantly filled, my manager lives on site and gets free rent for taking care of the property, filling units and collecting rents.