@Nathan Platter Short answer - no. 

I’m looking for a short term line of credit on a 4 unit investment property in Chicago.

I am in the process of renewing my real estate licensing and have been short sale negotiator in the past.I hope I can learn alot from this forum.

Do the math again (make sure to shop around for a bank with lower fees) and see if there is a solution to increases the value of it in a short time, so you can refinance it later after get a new appraisal after  rehabe....No deal is batter than a bad deal which will stress you out and not worthy of the time and $.  

Then take next best highest and use tenant and figure out rent per sq ft they could pay.You could possibly sell the land to an end user tenant, sell the land to a developer and make a spread, ground lease the land, or do a NN or NNN lease and construct the building.You need to analyze the tax implications of selling outright and paying higher short term gains capital tax versus developing and then converting to a new value created loan of 65 to 75% LTV.

Obviously I've got a short list from Google, but wondering if anyone has suggestions for standard cleanings and tune-ups?

So glad I did too, I love it here but I'm actually looking to move again, and Tampa is on my short list!

There was a few challenges as we were dealing with an extremely short time frame and he started with only a weeks notice.

There is no short sale here.

I agree, investing here in my backyard is ideal, especially for my first few times because I want to be able to get intimate with the end-to-end process and ideally be close enough to drive to my properties within a short time.