There are many posts here on biggerpockets about investors being concerned about the Chicago RLTO changes which state tenants can sue landlords for minor errors with the security deposit.

I would tread carefully 02,04,06,08,09,19,54 .Though they all have their good places.After I narrowed down block and brick in decent enough zip codes, I would view each address permit history for the latest upgrades or replacementsHope this helps

My concern is that I don’t want to be “low balled” or miss something on the deal, especially since this would be my first property.

Test this by typing any address you like into Google and look at the top pages that come up. 

If a tenant does not respond to the renewal notice that is sent with a self addressed stamped envelope enclosed, can the rent cost still be increased ?  

If you currently work with an independent agent and have a property in mind that may work, you could give them the address and ask for a quick quote.  

I guess my biggest concern is that it sounds like you're creating three addresses right before selling. 

I know the area well and condos haven’t done much of anything in regards to appreciation in the last 2 years, so I’d be concerned nearly all of your down payment will be gobbled up by commissions and closing costs if you sell, unless you got a downright phenomenal deal on the place or made significant improvements.

I just got a Toyota Highlander Hybrid; it is a very comfortable drive and the line has been out for years so knock wood any bugs have been addressed already.

Not impossible but will take some effort.As far as property management is concerned.