Don't fall for the seductive cash flow trap.  

Chicago is indeed a vibrant market with many opportunities, especially in the multifamily sector.Here are some tips and considerations as you prepare for your move and property purchase in Chicago:Research Neighborhoods: Chicago is a varied city with a wide range of neighborhoods, each with special qualities and investment opportunities of its own.

My current DTI is at 15%~ so there’s a buffer to cover the negative cash flow.

This property cash flows over $400/month, and has appreciated about $100K+ since we purchased it.

Get funding for 3 cash flowing properties with a DSCR loan 3.

My goal is to at least break even with my property and am prioritizing appreciation over cash flow.

I have been looking at 3 bd/2ba and preferably over 1800/1900 sq ft.I own a condo that I will be renting out which will be cash flowing ~500-600/month

After running the numbers, I would cash flow about $200 a month, based on no vacancies.

Columbus will likely see the fastest appreciation just based on the rate the city is growing, but in Cleveland you will see high cash-flow and Cincinnati is a great mix of both. 

Find deals anywhere in the metroplex which you can afford, then find reasons to exclude them from consideration.