A house hack ideally having your expenses paid by the tenants and you live rent free. 

Do a house hack first and live rent free.You can always learn how to estimate values so you know what's a good deal or a bad deal.

I want to live rent free so i can use my salary to save for another down payment.

I know that comes with all things investing....Are you familiar with any units available to live/rent out in Chicago/Skokie area?

Are you a transplant?

House hacking helped me live rent free (I didn't have the luxury of going back to my parents) and after I moved out, it was a great steady extra income from rent.

I am 31 and currently live/rent in Bronx, NY and work in Valhalla, NY (Westchester) as a Network Engineer.

25 and hoping to be able to buy a 2-4 unit building before I’m 30 hopefully in the next three years. Sold MF buildings the last 2 ish years so have a very firm understanding of investing but not so sure about the fina...

Meaning, for me to live rent free with two entire floors to myself and garage, with good commute to NYC, it's a superb opportunity, but if I try to rent that large space, I'd not get much money relative to space offered. 

I have family/friends all over the US and have had kind offers for me to live rent free while I tackle my next venture, wherever that may be.