We're glad to have you here posting. Sounds like you'll have an interesting trip however you decide to go. What part of Alaska will you ultimately go to? I've always wanted to do the trip you'll be doing via the Aleutians to Alaska so we will be very interested in hearing about your passages. Likely the trip via Hawaii will be an easier go, though.
Please do post an an on our Crewfinder once you've gotten closer to knowing when you'll go and the passage you will take