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.

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? 

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.

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. 

So that’s what I was simply saying was a moot point on the front end discussing with a seller.

I'm assuming it works by using this non-refundable EMD or they are simply daisy chaining.Ultimately, how can end buyers be most protected from fault of the wholesaler or property owner? 

Or simply to help the other LLC pay for expenses?