Here is the list:Asphalt cracks fix up – coding for drivewayRailing/ spindles for decks x 2 - both decks are about 8x8 feetPower wash for deckStain for Deck x 2Garage doors x 2 - need to replace bothAir conditioners – 2 - need to install new ones, the current ones are rusty and oldHeating system Furnace x2Water heater x1 - 40 gal Windows  – 2 lower level double hang 2x2 feet; 4 bedroom – double hang 3x3,5 feet; living room - 1 big window 4x4feet - steelChimney top cover x21 New toilet  1 New sink with the stopper  1 Fan for downstairs bathroom 2 bathroom fans1 Stove 1 Dishwasher Bathroom wall fix - about 20"x20"  drywall water damage next to the tubGarage ceiling fix - old damage, no leaks about  a square foot 2 Toilet needs to be tightened to the floor. 2 Filters replacement for kitchen fanKitchen cabinet missing 2 doors We are about to find all the pricing on all the things that we can buy.. but we do not know how to incorporate labor into this quote.

I'd opt for 3x furnaces and 3x air conditioners with heat pump if you're worries about bills.

I spent a lot of time up on the rooftop working on heaters and air conditioners.

Not major, but everything I have bought has needed a roof or new furnaces, or new air conditioners, (it's always something).

I was more thinking about going with some sort of ductless split with a 2 single units with 8 zones and setting that up with one to run for the top floor (4 units, 2 zones / unit) and one for the bottom floor (something like this: https://www.totalhomesupply.com/54000-btu-multi-f-max-multi-zone-mini-split-air-conditioner/p/LG-LMU540HV). 

The mini-split is essentially an air conditioner. 

As a landlord of a detached property, at least you can look at the roof or air conditioner to see if you might have a surprise bill in the pipeline. 

I hear chainsaws working on my trees, my new air conditioner system working, and the ceiling fans spinning like crazy.

I do not provide air conditioners in low income rentals.

We can temporarily install a window air conditioner, but hot weather is not the norm in our area and AC is not required, so most people do fine with just the fans.