The south and west sides of Chicago have historically had a lot of issues, and many investors have done well there.

The only issue is the interest rate is 7.125%.

We had a record breaking online attendance this week, hope to do the same next month:  Top 10 Title Issues Real Estate Investors have to solve with Accurate Title

However, the biggest con is that you are sacrificing a bit of your privacy by living right by your tenants and it is usually a lot more stressful since everything is your responsibility - managing tenant issues, handyman repairs, taking care of the lawn, etc.I would strongly recommend house hacking especially in the Columbus Ohio market!

An attorney that only does litigation or maritime law, not so good.

There's a good chance the issue(s) you face has already been discussed and answered.Ask questions in the appropriate forum.

First, there are about 6 states that I refuse to invest in because of their tax laws and what I consider to be an unfriendly business environment.

What is as important is that you require the insurance to be issued with you as the landlord as "additionally insured." 

We only disagree on what is basically a customer service issue.

I also wouldn't touch hilltop with a 10' pole. struggled. old homes, over budget renovations, lots of issues. realtors push people here since it's the only place cheap houses close to downtown can be good but homes are 1900-1920.