Phoenix, Arizona tops US in population growth more than LA, NYC.   

We could continue on with the roof Starbucks and become a brand...

I'm in a similar situation and I'm not finding any of these responses helpful :( Yes you can qualify for a va loan due to your military experience buuuuttt if you don't have continued income coming in once you're finished....who is going to loan to you?

Are you planning on continuing to invest in multi-family residences with family?

Debtholders get larger piece of the pie to continue funding the projects.https://tinyurl.com/ycjxcm8a 

You have an asset that in 5yrs time will be worth more (in theory) and you can always go to the bank to lend against.Plenty of wealth in Chicago so if you buy right you should it should set you up for good appreciation growth.

I don’t want the coffee shop to put such a draw on our real estate investing that it inhibits future growth.

We want to have monthly income crom rent and grow the equity.

Class of neighborhood, population growth or decline locally, job growth or decline locally, amount of new construction, percentage if home ownership but having watched rents since the late 80s on my parents houses and having my own properties for a decade or so I haven't ever seen significant declines in rent I have seen rent stagnation and rent growth but never any real drops out side of a couple areas where neighborhoods declined greatly.

The area in my opinion looks very promising for upward growth.