Certain areas of the city have outlawed airbnb but others allow it.

I have always been interested in home construction techniques that are different or older.Container homes, these sorts of shot-crete homes, bale homes etc.The biggest issue is not that fact that they will rent, for if they are in the right location, of course they will rent just fine.

Yeah, most cities/areas have a dedicated FB group like "XXX area real estate investors group" or whatever.

Quote from @Daljit Singh: Hi BP, I am currently house hacking a duplex in Union City, NJ, and unfortunately, the tenant stopped paying rent a few months ago. 

We help our clients:1) Find a fixer-upper to buy2) We get bids3) Negotiate a Scope Of Work with the owner using "Maintain to the Neighborhood" to avoid over-improving, but understanding we will have to pass city Rental Inspection to avoid being a slumlord.4) Provide multiple jobsite videos to show progress and document WHAT was done and the QUALITY.5) Handle passing city Rental Inspection6) Find a tenant with a Replacement Guarantee per Class7) Assist with refinance, so client can repeatSo, why you looking OOS again?

Parking will likely be your biggest hurdle.

According to the City of Chicago tax code, it costs $5.25 per $500 of the transfer price.

Biggest challenge was deal with my 1st eviction.

@Caleb Johnson one of the reasons the City of Detroit is like the "wild west"!"

I also talked to the city.