I don't see a way of figuring this out and worrying about it would bring on unnecessary stress.

I didn't think anything he has done was unnecessary or too expensive, he has always brought any repairs to my attention and has gotten my approval (no surprises).

You could just say you can't afford these kinds of things that you believe are unnecessary, but you can see it's very important to the tenant. 

The courts rejected many arguments, including the one that landlords should be able to opt out of S8 based on the administrative burden imposed by HAs.  

Don't start doing unnecessary things for a high-maintenance tenant, because they'll just keep you hopping. 

Notwithstanding the aforesaid provisions, if the acts constituting the discriminatory practice that is the object of the complaint are committed by the same natural person who has been previously adjudged to have committed acts constituting a discriminatory practice, then the civil penalties set forth in clauses (b) and (c) may be imposed without regard to the period of time within which any subsequent discriminatory practice occurred."

Post pics ASAP but, unless you've got a self-imposed deadline that you'll move heaven and earth to meet (which is what I did), give yourself plenty of time before you open your calendar for reservations.  

Liquidated damages clauses cannot be used to impose penalties, if I remember correctly.So, that's not going to fly in court.Plus, you need to check your laws, but in CA anyway, you can't include late fees in rent owed when filing for an eviction for unpaid rent. 

Both are too large and unnecessary for you, but with a spreadsheet and Trello I have ran a lot of other projects.

Now there might be an ordinance by the city that doesn't allow rentals or has put a moratorium on rentals for a certain time period.If the house is located within an HOA, then the association could impose a no rental rule in the CC&Rs.