So if it takes 10,000 calls to get one closed deal  that's $4k per deal which would still be worth it.

I think it’s definitely worth looking into.

How much is the property worth?

The increasing barrier to entry results in fewer new STR's coming available for sale, but also fewer options for guests to rent. 

Quote from @Louis Hamilton: The property is worth around 800,000 and has no mortgage on it.

If we are losing money every year, but do plan on holding on to it long term, with our goal being appreciation of the market and someone else paying a good chunk of our mortgage, is this worth doing on any level? 

I was chatting with some of my lending buddies at big banks and they are all backing away from the CRE space including office because operating costs are increasing more quickly than rents.

Quote from @Justin Brin: I created a heat map showing the population changes in each state over the past five years (2020–2024).The states experiencing the largest population increases are Florida, Texas, Utah, Arizona, and South Carolina.

By prioritizing five-star reviews, I built a strong reputation, which led to increased bookings and higher profitability.

Given his spending habits during his first term, it might be a wash.Costs to build new properties will probably increase.