Hey @Mordechai Chaimovitz - It sounds like you are talking about Chicago's NW side because there are definitely tons of areas in Chicago where a 2 flat can cashflow well.I know for me buying on the nw side was critical to my personal well-being and life happiness. 

Definitely on market.2) This is such a tough question to answer, but I think it might be something along the lines of don't overleverage.

@Devin Peterson Definitely always down to network.

Definitely do more research on the BRRRR method as that sounds like what you're trying to do.

Welcome to the BiggerPockets community, you're definitely in the right place!

To build a platform like that, you definitely need technical skills, but it needs to be informed by real estate domain experts as well.

I definitely want to align myself with a good brokerage and start building good reputation. 

Yes, definitely open up a HELOC even if you don't plan on using it.

But with only a dozen properties in only 2 states I’ve definitely not found a use for one yet.

The work colleague you mentioned was definitely incorrect.