So rather than overemphasizing WHICH market to chose, emphasize finding the right mentor/coach/team because it is possible to fail in a good investment market when you do not know what you are doing and to succeed in a more challenging market when you do know what you are doing. 

Pretty hard with a W2 job, but very possible... just takes too long.

Seems like I could possibly get a duplex with that kind of down payment. 

Show up at as many local meetups as you can to possibly meet the right seller, lender, or partner. 

It is possible to utilize low down payment loans and live in great neighborhoods in Chicago Did you work with any real estate professionals (agents, lenders, etc.) that you'd recommend to others?

Comps to me no longer play the only role because of rates, seasonality, etc., it definitely fights the arguments on re-fis with the appraiser but I'm noticing there's just a liquidity issue that is skewing things.I try to essentially start at the floor and work my way up on the ARV as opposed to seeing the highs and working it down.

From my experience working with over 400 investors, financing your first deal with minimal out-of-pocket expenses is entirely possible, you just need the right strategy.

@Stephanie SelbyRecommend exploring as many sources as possible to get referrals AND cross-reference them to get as much accurate information as possible.Check out NARPM.com, BP’s Property Manager Finder (BiggerPockets: The Real Estate Investing Social Network), etc.Also, encourage you to learn from the mistakes of others - by reading posts here on BiggerPockets about owners not having their expectations met by their current Property Management Company.

On the other hand, sometimes fame and celebrity can get somebody singled out to be harassed when they would not possibly have been at had they not been a high profile individual..

@Drew Sygit brings some good insight into the possible pitfalls.