First of all Dude....This site is for Geezers and Preeners. (Wannabes). Most people on this site don't leave their harbors let alone their hemisphere. But they are very good at talking about it and excel at criticizing.
I have said on this site many times that if you have sailed the Carribean you know that there are so many more kids like you on small boats than people on big boats. The big Boats you do see are owned by a cruising charter corporation. I say go get it and have fun.
When I was young I sailed the Carribean with a band of brothers in search of big waves. We had an awesome two years of surfing, diving and partying. I returned to go to law school. You are 100% correct that now is the time to go and get it. Good luck Chris.