As a professional mariner for over 50 years & someone who learned his trade on the left (west) coast, you might be MUCH better off to consider sailing to Hawaii & then to Seattle. As long as you go north of the Pacific high, the whole trip should be a breeze, pleasant & enjoyable, rather than a slog to windward all the way with very few safe places to take a break in.
I know the OI41 very well (one I delivered on from Great Inagua to St. Thomas; hard to weather in 25 knot trade winds) & it was not built to do a trip like that. It is an island cruiser.
Also, for the trip you are planning, I suggest you hire a top notch professional captain AND crew; you get what you pay for! I'd not like to see you trying to enter a barred entrance in 25 to 40+ knots of wind, with a less than top notch captain in charge.
I do not mean to put you off, but forewarned is forearmed.