I admire your dream, and you should hold on to it. Dreams are the fuel for our plans*.
However, dreams and plans should not be confused with each other. An out-of-reach dream can slowly grow into a plan as one acquires the experience and knowledge needed to get the dream into reach. You canât shortcut that process and start with the plan, even if you get help from others with knowledge and experience.
What I am trying to say is that you should not forget your dream, even though a lot of us have sounded very discouraging. But you should not let that dream guide you in your decisions and actions for now.
If you get someone to help you making a long checklist of knowledge, skills, experience and equipment you will need to possess before you do the trip, and you then start acquiring every piece on that list, your project will probably die. It will be insanely overwhelming, and you will hit plateaus where it will seem that you will never be able to sufficiently develop a required skill. You will probably also discover that you had checked something on that list because you thought you had it covered, but as your experience grows, you realize that you donât really have it covered, so you have to wipe out that check mark.
So what to do instead?
I will claim that you can get the development you need, just by continuing settings targets, which are slightly out of reach. For now, it can be basic stuff like self-rescues, an overnight camping trip where you bring everything in the kayak, learning to brace, etc. Later, it will be more advanced stuff like rolls, paddling in waves, adding some navigation challenges, etc. Later yet, you may want to learn to surf, do long crossings, etc.
And one day you will realize that you now understand the challenges of your Maine trip and are ready to take that challenge. You will probably still come up with a checklist of stuff you need to hone a bit before you are fully ready, but this time it will be your own checklist, built on your own experience.
My guess is that this day will be at least 5 years from now, probably 10 or more. But you will enjoy all those years immensely because you keep discovering new stuff to learn or practise.
(*: I just made that one up, but it is rather catchy, isnât it?)