It's probably a waste of typing on my part, since nobody in their right mind is going to be making this trip...
I can't think of any sailing skipper worth his
salt, unless he was on a very highly specialized high-latitude
boat and a masochist to boot who would transit the N. Pacific in these latitudes on a sailboat in October.
I know of what I speak, I also
fish in Alaska, but I do it in every month of the year. (I'm writing from my wheelhouse now, N. of Dutch harbor). I've spent 25 Octobers in either the Bering Sea or Aleutian islands, and I've had my butt handed to me on more occasions than I care to
recall at that time of year. This is on big
commercial boats in the 150-225' range, by the way.
Sailing E-W (or either direction, really) in these latitudes in the fall? Pure madness.
Like Jim said, though, if you've got the time, you could go the tropical
route. Otherwise, buy a ticket!
TJ