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.

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

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

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.

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).

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.  

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

The seller is in a unique situation and may be willing to work a deal with me that would help me make this possible.

So you can take that off the table.Buying an investment property first would be smart, but you can actually set yourself up with a unique option if you do it correctly.

I totally agree and will say that I communicate proactively with my tenants and provide examples of the increasing costs of property taxes, insurance and repair costs (labor and materials).My theme to them is “we must raise rents to keep pace with rising costs, but we are doing the minimum increase as we want to retain you our valuable tenant”..