I used to have a Minute sensor (for noise monitoring) in a unit located in a rough part of town, and guests would simply take it down.

From there, there still may be operational issues such as the  property being too seasonal and having a bad weather season or the market simply losing popularity.

Simply tell them they are in violation of the lease and need to do something. 

Even if it's not as good as you'd like simply hang on and then refi later down the road as interest rates come down with time.

You could also use tile - though not my personal aesthetic choice.

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? 

Talking to contractors and they suggesting to simply start over.

Simply put.

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

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