There are of course an almost unlimited range of guides,
books, etc. that you could be pouring over...altho' in truth, I think you'd be better off spending 5 hours on the boat for every one hour of reading what someone else thinks you should have or do.
Dashew's 'bible' is fine if you want to
research a system or a method or a
rigging option, but I don't think that's where the emphasis needs to be placed when prepping to move the boat down a river, down the U.S.
east coast, and then island hop into the Caribbean. 'Systems' aren't going to get you there, tho' they will make you a bit more comfy at times and give you more
work to do (and fewer dollars to do it with) as you install, integrate and then maintain them.
Here are two thoughts you might consider:
1. Find an old copy of Hart & Stone's Caribbean Guide (from the 70's). Read the sections on routing advice,
weather systems and seasonal variations. None of that is outdated and they did an excellent job of addressing those issues. Spend some time thinking about which areas you'll want to sail, and then develop your own
route and timetable. Understand that this will be an interative process: doing this will generate questions, which in turn will result in getting more info, and will generate discussion with the crew, which will have you revisiting both
route and timetable. This is almost like cruising! Good fun, and productive.
2. Do a little
weather research. Think about how you're going to get real-time wx info when you leave NOAA and then the cozy but limited Bahamas wx nets. Visit the NOAA web site and sample their products. Read a bit about
SSB radios, even if you have one and especially if you don't (e.g. get Marti Brown's
HF Radio for Idiyachts). Make some tentative decisions about getting wx info (based in part on Bruce's book) and then try them out on these BB's, soliciting feedback. Making your own informed decisions about wx conditions - and not being in a hurry - make all the difference in having a great time.
Jack