@Varun Sharma What Class of property/tenant are you expecting that will meet the "1-2% Rule"?

My strategy is to invest in C to C+ class properties that do well in good times and bad.

Finding good yields is tough in this environment. 

They will, and in today litigious environment thats a lawsuit. 2.

Some you will like and some are very 'pitchy' selling all kinds of classes and junk.Meeting people in person and getting to know them and what they do will help increase your knowledge that much more.

This could result in class action lawsuits where tenants of a building file together and basically wipe out even mid-sized landlords. 

What's the best steps/classes to take in Chicago to become one? 

It's all about realistic expectations.We've dealt with many newbie investors, that despite extensive chats with them to try & set proper expectations, buy a Class C rental - yet expect Class A results. 

If you're providing an "up-scale" environment and hope to attract more guests of this calibre (I do; they don't quibble about higher nightly rates and rarely cause problems) then I recommend white duvet covers and wash them after each guest.  

If you go into this asset class you are going to deal with court filings for non payment so that will be a pain.