I totally understand you. Holiday in the Caribbean is not the cheapest one for sure but you know what is ironic? When you actually live in these places, the expenses are (much) lower than here in Europe. Take Mexico where we lived, for example. We rented several apartments at different places during our stay. Some of them even had a pool, big terraces, some of them were literally just a few minutes walk from the beach. But they all were much cheaper than what we paid for an apartment in Prague. Same with food, transport etc. If you come to this tropical paradise as a tourist, it´s quite expensive because of the flight tickets, hotels etc. but if you come there to live, everything gets much cheaper immediately ;)
Happy to hear that you already managed to fulfill 2 of your 3 travel dreams and I´m sure that you will complete this hattrick :) New York is such a special place. I was lucky enough to visit this city a few times already. Honestly, I cannot stand all the hustle and bustle for more than a few days as my head starts to feel like exploding from all the perceptions but it´s always a very unique experience :)