I did extensive plastering of cracks, etc, repainting, sanding wood floors, new bedroom laminate floors, and new bathroom.  

You are a contractor .Well I have some news for you , I have to hire a painter to re paint , a lawn service to mow , and a handyman to replace the screens , and thats just what I see .  

I am overlapping my contractor repainting the place with the open house to shorten the vacancy time.  

Be prepared for total repaint and professional carpet cleaning to remove smoke smell.

So I have a rental property that needed it's fence repainted.

if all your leases end at the same time it means probably you will be repainting and fixing all houses at the same time, plus all your sources of income can stop at the same timewhat it the reason to align all of them at the same time?

I would re-paint, do whatever you have to do to get rid of the smell, and absolutely charge their deposit, just make sure you document what you bought (send them copies of the receipts), and send them whatever the difference is, if any.

Keep the rents up with the market, or at least sort of close to it.Say no strongly when needed-- No you can not repaint the house I just painted.

We had a rental outside of Philadelphia who had the same type of tenant (refusing to pay, more people living in that didn't, etc).Gave them a 24 hour verbal and written maintenance notice that we were Repainting /replacing the doors. 

I'd rather have worst case scenario like replacing the entire carpet or floor or roof, repainting the entire outside, etc... but how much do those usually cost?