Luckily, due to the number of items this person had at the home, we added charges for each day beyond the set closing date for them to vacate the property.

It is not an easy thing to run a property when your customers are horrible haha.I recommend student housing with 9 or 10 months lease and run STR during the summer for this property while students are on vacation.

@Jeremy H.since NNN leases are Signed with management companies that manage short term vacation rentals, there is a direct relationship.

I've also got a vacation rental in northern Wisconsin (between Minocqua and Tomahawk). 

While this may not apply to you, but with my CFO clients, the first thing I recommend when looking to invest, is to first look at a city/market where you either 1) currently or have previously lived, 2) have family/friends that live there, or 3) travel to for work or vacation frequently.Are there any markets that come to mind?

Cruising Right Along - Awaiting Sheathing Inspection.  

This is especially important for when tenants go on vacation for a week and turn the heat off all the way off.

I have several vacation homes and several local STR's my wife and I run. 

You're going to have to spend a bit of time researching markets but I think picking a market you like to visit is always good. every vacation becomes a write off! 

My husband and I have fixed and flipped one property about 3 years ago, and are looking for one to fix and rent out (and use for vacations) at the NC coast.