I'd also recommend finding an investor-focused agent in that market, sharing with them your buy criteria, and then having them set you up with an email list for properties that get listed. 

Plus, if you'd like to connect and talk marketing/sales happy to do coffee or something.Also, there are tons of Facebook groups for Chicago real estate.Lastly, just doing some 1:1 networking with lenders, agents, and architects is something we focus heavily on.

While it will likely give you more confidence and answer a lot of questions, I would say that talking to a seasoned investor, or even agent that works with investors, is a way better idea than spending 8K on something that you don't know too much about, especially before your first deal is done.

I am BP's Premiere Featured Agent for the WMass area.

I'm an agent in addition to being an investor.  

Hi, I'm a Broker in MA with just one agent in the company (my admin).

Sometimes I wonder if people just feel better about themselves to spend all those nights and weekends on real estate when, realistically speaking, they would have earned just as good a return (or pretty close to it) by investing in a stock market index fund and had way more free time in life  I realize my premise here is antithetical to the whole notion of BiggerPockets so of course bigger pockets hates me writing this, as do all real estate agents and property managers, but it’s the truth and everyone needs to think about it

I'm a licensed RE agent, contractor, and investor. 

Park Place Communities, LLC etc.) are created in Wyoming (and the address is a registered agent).

Personally, I’ve been looking for ways to align creativity with the numbers, whether that’s finding undervalued properties, building relationships with local agents, or pivoting to new strategies.