Looking for advice to invest a reasonable amount of cash

[David Davis]

Hey everyone.  Hope this is not inappropriate - I am a newbie:  What would advice would you give me for my first investment.  I have about $40k - $50k to invest?  I am open to house hack and buy and hold.  I live in Chicago and plan on staying in the city.  I own a small business so this investment is for my future.  Ideally, I would like to own enough properties to cash flow $120k per year - but that is a long term goal.  I don't need to invest all of my cash in 1 investment, but willing and able to.  Not sure if it matters, but I have purchased RE in the past.  I lived in a condo, sold it and moved into a SF which is under contract to close in less than a month.  Currently live in a rental apt.  

Again - I am a rookie so no thoughts are too basic or obvious.

Thanks in Advance