So I've had Dragonfly - my 26X since June of last year and it has been awesome

. I've been overwhelmed with fixing stuff and I am catching up a bit, now I would now like to bone up on the classroom and certification side. My queries on the web have confused me some. ASA has many classes and I like the sound of them, there appear to me many great organizations conducting the classes in an applied setting. Then there are US Coast Guard classes. Again entirely worthwhile; even essential.
My end goal is to be able to charter boats in other places in the world... and gradually improve my experience all while enjoying my boat safely as well.
I am a commercially rated pilot and I thought that there would be a more centralized certs and training method

...I guess not.
I am figuring to just start working through the ASA courses...is that a good approach? What would the learned members recommend?
Thanks in advance for your input.