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

I market them as basically a 'turn key small business'. 

If you look at Orlando, 365 market for the most part but it is one of the toughest markets to succeed in.

There's a website called intelius which allows you to do unlimited people searches in a 24 hour period for only about 25 bucks.

During solar peak time, the CAISO market also routinely sees generation from renewables exceed the total grid load, which is quite incredible. 

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

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

Based on your financing options, you are going to be limited to 4 units or under, given 5 and over become commercial lending, so no FHA or owner-occupied options.I am assuming you plan on living in one of the units, but to be clear, that will be a requirement for at least 12 months, under most mortgages.You may get other's posting about talking with wholesalers or trying to find off market deals.  

This is a real concern, especially in competitive markets.

Chicago REIA has over 800 member most don't do mailings or active marketing at all.