Do you need unique checks and balances in your away market so someone is representing your interests in the away market--yes.Slow and steady wins the race.  

Now, we do live in a small town, touristy area that does lack in nicer/unique short-term rentals. 

I don't have any answers for you Holli but I'm commenting so I get notifications when others reply to this as it sounds like a unique project and I'd love to hear more!

I truly have a unique situation as one of my mentors mentioned so I am trying to see what the best decision to do with what I have is.

I'm in contract on kind of a unique property. 

My business partner and I focus solely on making properties unique.

That is if you renew their 11.5 month lease for another 11.5 months you can only evict them for a violation of the terms of the lease (aside from a few unique carveouts such as you or a family member moving into the unit).

I agree with all of this HOWEVER I will say, if you have a unique product to offer to the market, you can attract even the highest quality tenants in the rougher areas, especially if they are secure properties that are close to downtown.

Is this a unique form of house hacking, where the rental income from our owned properties covers the rent of our new rental home?

A couple reasons for this include:US Territory:As a U.S. territory, Puerto Rico enjoys unique benefits not shared by its fellow Caribbean islands.