Multiple exit strategy possibilities:a) Traditional rental at current market rate of $1500.

The steps, licensing, regulations and everything are much much higher on option 1, however obviously would add a larger target market

It seems safe to assume there's a market, but obviously we'll need some more research to confirm that. 

My plan if i get the properties will be to Buy, slightly increase rents (as they are currently 200 behind market,) as tenants move out, renovate the properties with my BRRRR team in between ongoing Single family homes.       

You certainly won't get anywhere near the full market but you could maybe get enough to browse a sample of listings and/ or comps.  

I noticed the Chicago market has changed quite a lot since I started back in 2018.

In case helpful, here's more info on DSCR loans:DSCR loans won't use your income to underwrite the loan.DSCR loans are based off of down payment, credit score and either actual or market rents so it helps to supercharge an investor's real estate goals and net worth.Here's a bit more in detail about how rates are calculated for DSCR loans:1.

I agree with you that this may not be common practice in different markets, my experience with HOAs is only in the state of NJ.

Currently trying to isolate a market to settle into and focus on while figuring out why nothing seems like a good deal even though I keep hearing there are deals in every market (i.e., trying to figure out what I'm doing wrong while analyzing properties). 

The home appraised last year for 2.1m, currently on the market for 1.98.