I've only looked at condominium units so far but they all have exorbitant HOA fees which kill the cash flow.

If the building isnt a registered condominium yet then you'd essentially be paying "rent" to the builder.  

The median average household income in the US is 59,039 a year.   

https://www.bloomberg.com/news/articles/2017-10-26...By Patrick ClarkOctober 26, 2017, 2:00 AM PDTRents have increased rapidly across U.S. housing markets as the share of renting households has risen faster than the number of new units.

And proof that it is your primary residence is living in it for the majority of the year and moving utilities & other house hold items into your name during that time.   

For example, you could say that household income must be over $XX,XXX which would be above the threshold for receiving Section 8.... 

Life is short.Like all of you, we love rental properties for many reasons including it’s a tangible asset, everyone needs a place to live, it generates passive income so you can reach financial freedom and it’s a proven business model over thousands of years.All that being said, we have limited experience with real estate investing but have been involved with a few real estate investments including the purchase of two vacation rentals, a small office condominium and invested in a syndication outside the U.S.  

In my scenario, I am looking into buying a brand new condominium with no sold units yet.

Any comment about the condominium market in Chicago loop area?

It's a 1.5ba/2br condominium in South Florida.