If you’re just starting or want to minimize risk, house hacking is a killer move—grab a duplex, live in one unit, rent the other, and let it pay down your mortgage while you scale up.

This not only defers the taxes on the two rental properties but then once they live in the primary residence for at least 2 years that home now qualifies for the Section 121 exclusion on the gain.

My girlfiend and I are looking in La Grange and Brookfield which is not quite as fast west as you, but my aunt lives in Wheaton so I am quite familiar with your area.What's your game plan over the next two years? 

They're investing tons of money into those areas, and attracting a lot of good renters who work in the medical profession and will pay good rents to live close to their jobs. 

That was short lived!

Live in one unit and rent out the other three.

@William Taylor so many options...Use your RE knowledge to: WholesaleFind rental deals to sell to investors locally or here on BPStart leveraging your personal contacts to build your sales businessFind a motivated seller willing to do seller financing:- Move in worst room or basement, rent out all the other rooms for max cashflow- You could even live in the basement and STR the rest of the house

Usually living in it for a few years may be enough for it to cash flow positive when you move out.  

do you plan to live in that property?

The best projects I've seen from my desk are folks who are doing hyper-targeted, well-researched deals that are generally in higher cost of living (there are exceptions) areas.