NoWorries, I love your enthusiasm. I spent my first 30 years of life traveling around the world. I have been to over 60 countries, although 40 of them with the military, but the other 20 on my own accord and dime. That said, I love your mentality, it is mine as well. Life is short, and doing the crossing you are thinking of is going to be another great chapter in your life. I am sure that our predecessors were quite literally in the same boat, to go or not to go. Greatness comes from the unknown, as does danger. But if you do not go out there like that, then life can get long and boring. Kudos.
Seb5thman, I would say that you are doing well on the education. If I were you, I would do a bit more practice. I myself am a beginner and I took a 36ft out today, largest ship I've skipped, and it was a hell of a good ride. That said, I am sure if you chartered a bigger than 22 footer, you would do great. I mean, at NoWorries age, I would have taken too it in a Catalina 22 no prob, but at my little more seasoned (only 31 but things are starting to hurt, maybe I should slow down playing rugby) age, I am learning that more sturdy built boats sure handle much better in the Pacific. Like Jimmy once sang, you got to treat her like a lady.
I am rambling, but I guess my point is, go for it. In the end, you will have a great adventure and a life time of memories.