Personally I think there are great opportunities in Dover, Somersworth and Rochester. 

We have an area of town where AC unit theft is common but I don't think anyone is pulling them out in-between occupancy.

Lending to Entities Only: (Not required but think carefully.)

Based on rent of $1,695, I think you'll be lucky to get an appraised value of $160k with a CoC return well under 2%.

Instead of evicting them, i was thinking is there some way that I could rent it back to him for very cheap (mainly to cover just the taxes/ insurance) ie 2k a year rather than the going rate of 2k a month for similar properties.

And I don't think it is as clear cut as people are saying.

Most professionals will recommend a separate LLC for every $1 million in assets, but I don't think that's necessary.

A couple other neighborhoods I like besides the two you mentioned are Washington Park, Hyde Park, Woodlawn, and South Shore.I think that area will continue to be gentrified because you have the lakefront as well as CTA trains.Is there any reason you are targeting Chicago instead ofdoubling down in Kansas City?

I would love a ideas on what you think might be best to do in the current market and may even be interested in partnering with someone if the numbers work for both parties.

I would slow down and think about your BUDGET, what you can get for $30k, and how you can increase your income.