The offers I'm getting are off market offers through a broker.

Agreed with Stephen, I dont know your market but we have many illegal multifamilies.

Off-market property, which is likely the case if you were buying from a wholesaler, has no financing or appraisal contingencies most of the time.  

More markets are creating "Good Cause Eviction" laws designed to protect tenants from unfair evictions.

I'm overwhelmed by which market(s) to choose. 

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I am not a lender but I work with a lot of buyers who utilize second home loans and I am 99% sure you cannot buy multiple second home's in the same market. 

This means researching the market, understanding tenant demand, and ensuring the cash flow comfortably covers the loan payments.

Is this common in the Chicago market or markets with high property tax? 

It's a function of the market cycle.Great postGino