Also illegal for the entire school year, if the tenant has kids in school. 

I am not a tax adviser and barely graduated high school so I am not sure if I would listne to me. 

I'm in South Loop near the Loop, lake, Grant Park, CTA, and a variety of hospitals / schools, so renting out the room on a mid-term basis (32+ days) for a premium was the best strategy for me.

I like option 2 to diversify the investments in 3 smaller rental propertires, 3/2 around 1500 sqft, in good school districts which will open the biggest pool of tenants. 

Battery Park City Exchange (New York City): The city of New York engaged in a land swap with the Battery Park City Authority, allowing for the creation of a new public school and affordable housing units in exchange for a parcel of land that was then developed into a high-value commercial property. 5.

So they work a full time job and go to school full time. 

I briefly worked in commercial lending after I finished grad school and that really opened my eyes to the inner working of that industry.

We currently have 10 single family properties in the best school districts and we self manage.

I am not going to move into a dormitory style house and raise my two year old in a location with poor schools and incredibly dense housing, unless I have no other option. 

Good luck, you are a busy man with school, family and baseball.Likely your best bet is house hacking (if your partner and child are willing to share housing).