Since this is a second home/vacation rental, it wouldn't make since to have multiple properties in the same destination (ex. not owning 3 properties in broken bow), don't the 10 properties need to be spread out? 

I also know it has good proximity to destinations like Lake Mary, Mt.

There’s a long, twisted road of lack of communication, a “property manager”, a tenant (not mine), a landlord, and 2 plumbing companies upon which the destination is my current dilemma.

Our goal for the property is to turn it into a popular Airbnb location as well as a destination wedding venue.

I would choose this property mainly because it is already a tourist destination and there are areas already established for short-term rentals and have regulations in place. 

Working with several of her agents now between Blue Ridge, Smokies, and the Destin area.

Disney area, Destin.

Buy him a bus ticket to a new destination he would like to go. 

At the end of the day, Bar Harbor/Acadia is considered an exotic destination because of it's not the easiest place to get to for most people.

However, if you have the means, commercial can be very rewarding once you put a property on "cruise control".Just one person's opinion, but I hope it helps!