typical charge in chicago area is $4,000 for brand new furnace and air conditioner 

Sidewalks will not be being pushed up by over grown roots and air conditioners will still have plenty of life left in them to get several decades down the road. 

The home inspector warned that I would probably need a new air conditioner in the next few years, so I planned to start saving all my cash flow as soon as I got tenants in.

It looks like the new standard for air conditioners is freon free.  

We also provide our guests with basic toiletries (mini shampoos, conditioner, soap, shower gel and lotion, makeup remover wipes). 100 pcs cost about 100 in total.Make up remover wipes were huge so guests do not leave stains on our towels.Each guest gets a bottl of wine when they arrive.

Is a tenant a jerk tenant when they file a complaint against me with HUD because I take weeks to repair an air conditioner in one of my Phoenix rentals in July? 

What if the tenant destroys the air conditioner, let's say with a hammer, and then demands that a new one be installed at someone else's expense.

I've had many vacant properties in Las Vegas that were in escrow when thieves stole the air conditioner condensors, every appliance and never had an insurance company deny a claim because the property was vacant.

A properly setup air conditioner is supposed to remove moisture from the air.

BTW, removing the air conditioner is not legal in TN either.