If you ask anyone in this business, note servicing is the Achilles heel and it is extremely difficult starting one from scratch. 

You need to identify which strategy you like best before jumping in and get extremely familiar with the process of underwriting deals.

I am extremely outpriced in my market, and I am a first time home buyer.

Your wanting to do high-risk via extreme leverage....via high risk OOS investing, committed to never being boots-on....... via high risk class c....... doing reno's to make habitable which is high risk at a level we should just call it EPIC risk..... 

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!

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.