I’m aware that money is likely going to be spent but, assuming it doesn’t, then can you still make tax free cash flow simply off of the recurring deductions like interest, management, hoa, utilities, taxes, insurance and depreciation? 

Many national parks out west are lacking in lodging, some are rather seasonal, but I feel like there's a lot of untaped markets out there. 

Those guest protection policies for most other channel managers are simply priced as a flat rate <$100 per stay insurance policy.

Simply put.

Simply put, does anyone have suggestions of how to dispute this with the city?

There are going to be three levels of addressing this 1) things you can simply go there and do anytime (pick up pet waste and throw it away) 2) things you can do given proper notice (enter the unit and inspect, repair damage etc) and 3) things you can only do given proper process/procedure (notice to vacate, increase rent etc.)

I don’t see how he could simply independently come up with such a high price without discussing it with me first. 

I believe shared housing is going to become more popular, due to the lack of available housing throughout the country; and lenders, insurance, etc. will need to find ways to accommodate their use. 

Ironically most investors don't slow down to ask themselves that simple question but will prepare a multi tab excel spreadsheet justifying the reason behind purchasing the low barrier home that lacks fundamentals because it meets the 1% rule or is a good BRRRR candidate because that's what they are taught.

Lack of water?