Have a competent attorney look into the concept of adverse possession, or perhaps an action in order to quiet title .Adverse possession allows you, in this case, to claim that property as belonging to you, because of the criteria that have been seemingly met over time.

Once emotions take over you can lose control of the rational thoughts, which can lead to bad business decisions.  

A little bit about me:I live in northern Virginia, am working towards financial independence, might get married in the next 2 years, and believe that most of my wealth generation will come from something outside of real estate.My predicament:I really like the concept of house hacking and how it can reduce my monthly expenses. 

I think it is all about perspective. if there are successful investors in CT (which I am sure there is) then the proof of concept is there its just about playing by the rules and finding your competitive advantage.

I am very new to the concept of wholesaling and have no real estate background.

Normally the rent would be paid as usual, and the pro-ration would be done in the closing accounting along with other prepaids like taxes etc.

I would start with a trusted and recommended real estate attorney in Costa Rica to discuss the concept they often use of a Corporation owning real estate in Costa Rica. 

We understand the basic concept of rental investments we are looking for homes and are pre qualified already with a high 4 to 5 % interest rate.

I submit that I don’t know and no one else does either.So do you buy Bitcoin now because it is down 50% from its high or do you wait because $30,000 is just a momentary pause on a continued steep decline.Real estate while more predictable than Bitcoin is similar.So buy property that is is good value today - with reasonable rational reasons for optimism for the future - and wait.

I think you've confused a couple of concepts here which all address first.