Key West Vacation Rental Deal Analysis - Am I missing something

[Jack Bradham]

Hi All, 

After many years of hoping and wishing my wife and I have committed to trying to find a place where we fell in love... so many years ago. Key West, FL 

So there is some sentimentally here. (Big Time) But, I am trying to at least not lose money. I am looking at a town house and the price is roughly $1M. By my math I will lose 2k a month.. lose. 

Here is my spreadsheet that I am working with. I verified as much of the data as I could through AirDNA and Mashvisor. 

https://docs.google.com/spread...

I feel like I can not so math. And I know I can.... am I overdoing it somewhere. Negative thinking some how.  

I'm asking myself. How the @#$% do people make money in this market?

Couple things to know: Only some properties in Key West have STR licenses (transient). This property has a modified one that allows for 26 weekly rentals through out the years. Based on my understanding it is good enough for filling up the year. HOA covers insurance which is very expensive here. I live in NC... remote management may not work out.