Also, if I move out in a few years, renting the entire condo would profit me at least $400/month (based on current rent prices, which increase pretty rapidly in Chicago).Are there any tax implications to this?

Right now I'm looking at a MONSTER of a deal that I need to move rapidly on, I need to know the general concensus on my idea...

Not sure if this will help but...If you have documentation (letters from the creditors) of your pay offs, or if you pay your credit cards down to 30% or less of the credit limit and you have documentation of the new balance or if you have documentation of things being reported on your credit report that should not be there, you can give this doumentation yo your morgage brooker and request a rapid rescore for a fee.http://www.newhomesource.com/articles/rapidrescore.htm?

Right now I've looked at Lansing, Rockford, Grand Rapids, Traverse City, and Kalamazoo as possibilities. 

Rents have been rising rapidly in our area.

It is difficult to to make LTR work in Austin because of the rapid appreciation we've seen so I pivoted to doing medium-term rentals.

We saw inventory tick up a little bit in going into Q4 last year, then decline rapidly.

Are you trying to building a portfolio rapidly with a small amount of cash? 

Live in the Grand rapids area with my family and a house that we bought one year ago.

Or if appreciation will be tamped, but rents are rising rapidly with no end in sight, same scenario.