I hope this doesn't detract from your post, but I am on the other side of this same equation and have some related questions.

Are you doing it full time or do you work a side job?

This location is considered as "the wrong side of the Troost". 

of condos / apartments / townhouses listed within a relatively small area on the North Side (River North up to Lakeview) which makes me nervous about the potential for oversupply within that market. 

On the flip side, students can sometimes cause more damage than your average renter, so make sure you're asking for a deposit that will cover you if they destroy the place and always make sure you require renters insurance.

Cleveland has seem to be hot for a good while now.

I plan on taking to an attorney and double check on this for Washington before I get started just so I don't find myself in hot water.

I know everyone talks about how their market is crazy hot but for example a 2 family house, that's behind another house on the same lot (aka. no yard of any kind) just went on the market on my street for 1.7 million.

They could have been a real pain in your side with this dragging on for 5 weeks during summer.

If I had 50 houses right now I could rent all 50 with this hot rental market we are in.