I intend to rent out the units by room to college students (does it sound like this would work in this area and what are some general tips/things I should look out for?).

We go above and beyond when it comes to protection.. starting with insurance coverage, sings in the listing and in the property that there is no guard on duty (as silly as that sounds), putting extra locking device high enough so youngsters can't reach, an alarm/beep system to alert them that door opens for those with small children (or elderly) so they cannot wander out in the backyard with no one noticing and risk drowning.

The whole "he's open-sourcing everything for the world" thing sounds nice, but in practice, a lot of those ideas haven’t exactly panned out the way he claimed they would. 

Sounds good about connecting in the future.

Real estate success is driven by demand, it sounds like you will have more tenant options and higher prices in Ft.

Hey @Mordechai Chaimovitz - It sounds like you are talking about Chicago's NW side because there are definitely tons of areas in Chicago where a 2 flat can cashflow well.I know for me buying on the nw side was critical to my personal well-being and life happiness. 

Referrals from local investors on BiggerPockets can be a great resource. https://www.biggerpockets.com/business/finder/agents@Mark Ainley sounds like a great person to link up with!

As an aspiring investor I am at the stage where I am looking to learn through mentorship.

It sounds like you are off to a great start already especially by educating yourself! 

I'm not familiar with Cincy but it sounds like you have a good foundation in place.