Investment grade deals are found off market and you have to do a ton of marketing.

@Doug KienzleDon't forget to take property taxes into accountAround hear( Cook County, IL) anything below grade would not be factored into assessed value.

Hey Jordan while on your search for a Property Manager I figured you'd also like some more resources on the Cleveland market itself so I have linked in The Ultimate Guide to Grading Cleveland Neighborhoods for you and your friend.

Here is a link to The Ultimate Guide to Grading Cleveland Neighborhoods.

Considerations I have are grading the lawn, making the grass one uniform species, and possibly repairing/redoing the concrete areas and even extending the single lane driveway to make room for a second car.

I have included a link to a gif showing the location grades of the neighborhood and surround areas from 2015 to 2018.

Should I 1) Move out of my current duplex getting a non-owner occupied investment grade mortgage on it and get a conventional mortgage on the new one(requiring a lower down payment)?

I think my grading of neighborhoods may be skewed by living in Franklin my whole life. 

And a neighbor trespassed and illegally graded part of the land to divert the flow of water away from his property.

For that I created The Ultimate Guide to Grading Cleveland Neighborhoods.