everyone wants the distressed assets you're trying to find.the short answer to your questions is: start going to lots and lots of meetups and network in person.i would also think about house hacking as soon as you can. 

house hack is possible. base way to get feet wet

Starting with house hacking is a smart move, especially in a higher-cost area.

I didn't have much imagination for it. 5 years ago I started looking at buying a larger home I could house hack because it allowed me to get a larger property than I could afford.

They can be problematic for guests to use, rely on connections with other devices that can fail, and are often easier to hack than a key lock.

If you are just getting started here in Chicago, house hacking is the ideal situation.

@Michael Davisstart with a house hack

I specialize in small multifamily properties and house hacking working alongside BiggerPockets podcast guest Andrew Freed to help investors find high-performing deals in Central MA.My Background:  - Started in late 2019 I utilized an FHA loan to get my first 3 family property in Fitchburg, spent about a year fixing it up and soon after I refinanced. 

We bought it in 2016, did nothing to it and made $40K, which we turned around and used to buy a duplex to house hack. 

Also, I am assuming since you house hacked that you only did 5% down, which then increases your mortgage payments compared to 25% down buyers.