Renter population, landlord friendly laws, key industries, growth and endless other indicators. 

Looking for investors to partner: Endless opportunities.

Downsides are having to get registered with section 8, annual inspections and of course some tenants who won't treat your property well - but we all know that possibility exists with any tenant - just see the endless threads here about the crazy stuff people do.

Nevertheless,  Chicago has an endless amount of old small multifamily buildings that are in need of renovation, plus it offers purchase prices across the board.Outsiders will (or insiders for that matter) will complain about taxes and crime, but there are + and - in every market.  

You can also hold a one-time open house so you don't have to have an endless amount of showings.You can try screening over the phone or Zoom or something so that may be an option as well.

I’ve been researching strategies, and the options are endless.

Here are my favorites:Rich Dad Poor Dad - getting your mindset right and shifting your thinking to getting your money to work for me.One Rental at a Time - how anybody with a W2 job can get to financial and time independence.The Book on Real Estate Investing - understanding what real estate investing is.Profit Like the Pros - motivational and inspirational stories of the endless possibilities to get great real estate deals.Happy to talk about other resources, tips, tricks and anything that helped get us started.

Without knowing what the specific requests are, I really cannot comment on this, other than Helath and Saftey issues should be fixed immediately (such as bad breakers, endlessly dripping faucets, etc....

Are prices too high, is a crash coming, we're teetering a recession so should I hold off... the list is endless, and it never goes away completely.

Like I said, the options are endless.