Follow the local licensing and disclosure laws.

Going to start by checking into local REÍ meetups and talking to some friends and family that are doing what I’d like to.

Nevertheless I am local now and I have that real estate desire (which never went away).

So going to attempt something more local first. :)We definitely want to invest in true vacation rentals as well but this will be a good learning process with not as much risk to start.  

., but there’s some good news for renters: local rents have dropped to a 3-year low, with decreases of up to $200.

Find and attend your local REI groups. 

Go to BUILD YOUR TEAM at the top of the screen and look for local investors or meetups in your area.

@Jennie Berger gave you the whole kit & caboodle on Chicago zoning so I don't have a ton to ad, however, I'd highly encourage you to engage an architect like @Samuel Pavlovcik or @Prashanth Mahakali, both are awesome local Chicago resources.

More relationship underwriting with local banks.7% interest, 25yr am, 20% downEasier to scale, easier to manage.

For instance, many tribal lands are exempt from state and local property taxes, which can obviously lead to significant savings.