This is a very lengthy question to answer.
Yes there will be some windward work and at time you may want a little help from at least one of your engines to help with the windward work. (Old habits die fast when beating days on end in a cat). There was a time when I refused to use the engine. However picking your weather is obviously also a big factor in your comfort so hopefully you will be blessed. I suspect you will just come up the eastern chain stopping when you want. The islands are not that far apart so some good current whether information will be a necessity.....say with a sat phone at least. As far as what islands to stop at or bypass would be your choice cause each have their own good and bad. I personally love them all and would not begin to say which ones to avoid. However certain harbors within those islands yes but maybe in another letter if you are interested.
Sorry so have to go now but....to be continued!