So I know multifamily is the largest part of the path, but we're new to the field.

@Dinardo Rodriguez - You've got tons of great feedback above (@Henry Lazerow stole my thunder that Chicago landlords pay water, sewer, garbage).I think you are definitely on the right path, doing the right things, and asking the right questions. 

You're on a good path here and I want to encourage you to keep going!

In my part of the country, you have to put a mobile home on a cement foundation if it is not in a park.

All 36 SFHs homes in my portfolio required 20-25% down with an average purchase price of $270k but the path to scale comes with inevitable financing challenges.

Country Hill's, IL or Park Forest, IL.Would love to hear some thoughts from the pros here.thanks !

As you may know the whole country has a major housing shortage, which is why rents are increasing. 

I believe La Pine is in the path of growth for the Bend area and prices here were 100k-200k less for comparable homes.

I can connect you with the right PMs, Roofer, Plumber, Electrician, General Contractor, Title company etc. and helped you avoid the mistakes that I did when I just started out in this part of the country.  

Otherwise, I'd focus on the hill country and the lakes west of Austin for better STR locations near the Austin area.