My biggest concern would be the location is not that interesting for a “vacation” per se.

Then the Sheriff will post notice and they have 10 days to vacate. 

@Ana Brasher,There is no official declaration or form that is required by the IRS or your state Department of Revenue when you start using the vacation property as a rental. 

We plan to start with short term vacation rentals, in multiple locations around the country, then possibly move into other disciplines from there.We are happy to be here and learn all we can.Aaron

I know the vacation rental market has a bunch of pricing tools (pricelabs, airdna, etc) is there something similar for the hotel industry? 

Look at true, regional, drivable vacation markets instead with established STR presence 

I specialize in multi-family properties and have a lot of experience as a buyer's agent, specifically for people relocating as Traverse City is a vacation town.

We are currently looking for a vacation home that will double as our first STR in the Orlando/Davenport area.

Or ... you could take a free vacation.

Many New Yorkers are choosing to purchase vacation homes in this area, particularly along NY Route 17 from exits 106 to 99.