you may be dumping a lot of money into it then to value-add. is the property close to transportation for people ( bus, train). just a couple of things to consider.

Transportation is a major issue here.

Transportation to NYC is great too.

I would also consider Logan Square, Avondale, Irving Park, and Portage Park, they're all close to the highway, and you can get to nightlife via public transport.

I was thinking that if I could find a place close enough to public transportation, I could cut down on my living expenses utilizing the aforementioned owner occupied multifamily home strategy, while maintaining low transportation costs. 

Mass transportation, parks, schools, and etc.

Whatever city Amazon picks will be interesting as I see techies needing entertainment, convenience of Ride Share companies and food deliveries, healthy political outlook from their politicians, and easy commute from airports to public transportation systems as they don’t Like owning cars.  

Rent out Transportation: cars, trucks, bikes, hell even a scooter.

so I say check out CL.. and find a used shed, and transport it to your house and make due for the 2 years!   

So we'll try to negotiate a slightly higher number and let our tenants know there is public transportation coming.Again, thank you for all the info!