I just don't see you being able to do a whole lot to allow you to sell it quickly outside of lowering your price to something extremely compelling.  

If you purchase a rent ready RE investment this could be 0%, but at the opposite extreme a good brrrr can produce the now elusive infinite return (I have achieved this on most of my RE investments but believe it is very challenging in the current market to bp not be cash negative after the refi to extract the added value.I expect to make an offer this week.  

If I did set out to invest in the local area, I would scrutinize the numbers like crazy and be extremely conservative with my estimates.

@Chris Kay finding a quality, cost-effective contractor is extremely difficult:(There are thousands of contractors that are great talkers, but rarely perform within budget.Standard bait & switch is to lowball a bid, then once they get started all sorts of things "pop up" that somehow their bid didn't cover.

Even the most expensive property managers are EXTREMELY cost effective if you really think about it!

Gatlinburg and Pigeon Forge are both extremely strong right now , with most people overpaying in the years that you mentioned and simply not KNOWING OR CARING  how to properly run a top notch Air BNB. 

I think one of them offers a public API.Once you get your license, you can join the CAR Chicago Association of Realtors and I have found them to be extremely helpful with questions like this. 

Extremely helpful and constructive post. 

Section 8 rentals are frequently located in extremely low barrier of entry markets, especially the single-family homes and small multi-family properties which I assume has also led to an influx of inventory.

Verifying last 2 years of rental history and income extremely important to find the “best of the worst”.Make sure you understand the Class of properties you are looking at and the corresponding results to expect.The City of Detroit has 183 Neighborhoods we’ve analyzed.PM us if you’d like to discuss this logical approach in greater detail!