Re: Cruising Skills/Practice
Your trip sounds awesome, and you sound like the sort of guy that's going to take preparing for this seriously.
The only thing I'd suggest are some shakedown cruises while you still have a car and money and place to park the boat and work on things. I'm still a beginner; but what I've learned is that pretty much any problem is solvable, if you're sitting at a dock with money in the bank. But that's not necessarily true when you're seasick and pitching in the waves out in the ocean when something important is broken.