I can't speak for your local market conditions in Chicago as I primarily operate in San Antonio, but as far as the pros and cons of those two options, here's what I have:Multi family house hack is the lower risk option, with the downside of a lower short term return, as well as you having to wait until you have more saved up for the down payment.The small single family flip probably has a touch more risk, but if you find a willing partner on the deal you may not have to wait as long, and if your flip is successful you'll get your return back much sooner. 

@Ellis San Jose thanks for your insight.

I've worked with several out of state investors for the San Antonio market, primarily as a wholesaler.

I have a house that I’ve owned for a couple of years in San Antonio Texas.

In the long term San Diego RE has always risen. 

I am a full time sailor in San Diego, (please don't thank me for my service I'm just a regular person like the rest of us), part time realtor, and I'm also an aspiring RE investor.

Most of my clients in San Antonio purchase deals with a cash or hard money loan, but for something you're occupying yourself a FHA loan is appropriate.

The San Antonio market I operate in is known for massive appreciation.

Coffee on me if you're ever in San Antonio!

Does anyone have a recommendation for a real estate attorney in San Antonio?