Of course capex does come into play, but I have a lot of factors on my side including most major components of the property have been replaced already, including roof replaced 2 years ago, water heater replaced 3 years ago, full house was just repiped, septic system is 5 years old, HVAC system replaced in last 7 years, i do not cover appliances with warranty in my rentals, and the tenant I placed in the property is a single dude who works 60 hours a week and just needs a place to sleep.

Meeting with a real estate attorney is the right move, as they can confirm whether the HOA’s claim holds any water.

Do I need to contact the city of Chicago to have the water shut off or is this something I can do myself? 

From, "someone ate my food" to "someone takes long showers and uses up all the hot water" and even arguements over parking spots.Who wants to handle all that extra nonsense for "free"?

Most of your issues sound water related.

There are some great deals up in Pensacola where you still buy a 2/2 on the water with a boat slip. 

. - Evidence of water damage in the basement. 

What is the cost of an HVAC system vs. a heat pump vs. forced hot water vs. baseboard and what is the cost to the tenant? 

This includes incentives for green building practices, renewable energy adoption, and water conservation measures.

Usually as long as their are no life threatening issues (no HVAC, windows won't open, no hot water), the housing authority will began to pay the rent and give you time to address the required repairs.