I recd a bunch of marketing flyers from them last week

So overall experience of your QI to work in a number of markets and locations is really the key. 

As you embark on this journey, you'll learn the importance of market research, the art of negotiation, and the power of leveraging assets.

I was studying the market and my rent will be just enough to cover the mortgage and HOA fee now I might to pay out of pocket for insurance but don't want to sell it yet because the area is growing and might have good appreciation in the years that follow.

It’s exciting to hear about your plans to dive into this field, and Chicago is a fantastic market to explore once you move there.It sounds like you’re on the right track with your interest in House Hacking, Mid-Term Rentals, Short-Term Rentals, and the BRRRR strategy.

You should start with a focus on a 2 unit multifamily property in a market that you can afford to get into. 

While we are not immune to market shifts, we typically don't see huge bubble bursts. 

,  occupancy rates, capex plans, competitor rental rate study, market study, etc.  

Very solid market, been investing there over 10 yrs and the rents continue to climb! 

Look for motivated sellers off market and market via cold calling and or direct mail, geofencing, advertising and the like.A good wholesaler is as @Ericka Parrott mentioned, direct to seller, did good underwriting and can deliver an actual "Deal" whether buy and hold or flip.