Chicago Garden Units and General Market Questions

[Joshua Branovsky]

Hello BP, first time posting here. I will be moving to the north side of Chicago this summer around the Evanston area and want to buy my first investment property (I have tons of questions). My plan is to house hack using my VA home loan, I don't realistically see me getting cash flow while in the property and I'm fine with that.

1. I see a lot of these non-legal garden units that are finished. Does anyone know how these work regarding owner occupy, making them legal, whether my lender will allow me to live in it, and any other information about them?

2. Does anyone have any advice for the Chicago market in general?

3. Is my house hacking strategy a viable option? I will attach an example property I'm looking at in the area that has a non-legal garden unit. Although, it is probably a little out of my price range (400k-450k) 

https://www.zillow.com/homedet...

Any and all questions/comments/concerns welcome!