I'd be very concerned about the HVAC, plumbing, outdated electrical, or old windows.

Paint, LVP flooring, IKEA cabinets, replacing outdated light fixtures will save you money if you do it yourself and they aren't highly technical. 

If they don't like it, please provide your move out date.

Can it have an open move out date, saying that last date depends on move in date for new tenants?

We are updating/upgrading all outdated units as the leases are turned over.

Tenants left the washer valves on when moving out causing serious damage when Water Authority turned the water back on. 1) Tenants disconnected the water a week before the move-out date without informing my PM.

There is a ton of outdated inventory at all price points in Chicago which is a reason I like investing here.  

Lighting- outdated lighting can make a place look dull and unfriendly.

There is a very old, outdated, but functional 2/2 1782sqft house on the property that i am currently using as a woodshop. 

You might get stuck with a horrid lease...on outdated technology.Set a limit.