In a crowded market like Orlando the recipe for success is simple, Focus on the client experience and that begins with cleanliness; Have a well-designed and themed house (you don't have to go crazy but try to be unique); Have Amenities to offer, there are a bunch of communities and the amenities they offer are powerful marketing!

There are unique tax laws when you are house-hacking so make sure you work with a professional who understands them.House hacking makes your tax situation more complex.You purchased a property that is treated as both an investment property and a personal residence.

Any unique challenges anyone has run into?

This is a unique strategy.

Hey Jake,Posting here is a great start, there are many different kinds of masterminds in many different niches.

It is a specialty policy that covers the unique risks  of a vacation rental.In the Smokies, the gold standard is Southpoint Risk in Knoxville.  

Uniqueness is key also.

It presents a very unique opportunity to detach it from the city limits to remove undue restrictions that have affected the value and use.

Etc...i would always have a sewer line camera as well.Maybe others for unique properties.....

Depending on your niche, you could be easily stay busy with whatever it is.