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.

Over the last 16+ years of working with investors and property managers, I have encountered only two with this skill.You can identify a tenant segment with a high concentration of reliable people through property manager interviews.

We are very familiar with the area but need advice on how to identify potential opportunities and analyze the deal as an investment property. 

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'm can record a Loom video response for you.Like any business model, you have to start with identifying the customer and where the demand is.

I think identifying these markets that have a history of vacation rentals (so STR regulations are not worried about), near State or Regional Attractions (alot of national attractions may be priced out but not all), while also being affordable for the average STR investor.

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