Better to concentrate on decreasing expenses and saving for now. 

Sometimes letting them do their thing can save so much time and stress!

From what I have heard, Dayton is a similar market, and you will ALWAYS save money by investing locally by not needing to hire a Property Manager (yet).

Building a trusted network of contractors will save time and ensure consistency as you scale.

I feel I have a rough idea, which is..I'm in Rogers Park, my next important step is to wait out 1.5 years until I can fully rent out the condo, but for the meanwhile get a roommate to save more money.

I have about 20,000 saved and will be looking to make an investment in the following year.

They tell you you’re asking too much rent (you lower rent, avoid vacancy and make more money) ,your marketing is bad (they take new pictures, advertise in different places, change wording, whatever, and get a tenant saving vacancy.)  

I don't know how much money tenant has in checking / savings / 401K, etc.

It depends on what the terms of your mortgage are.Pros-with no mortgage, you have higher cash flow.Cons-if you plan on buying more properties, you are better off saving the money for a down payment for your next place.The big questions are: can you get higher than 7% return if you invest that money elsewhere? 

So yes you can exchange it to save capital gains taxes on $266k plus 19 years of depreciation recapture.