If you plan on taking the slow route
north, I would definitely have experienced hands aboard, knowledgeable about crossing the Columbia Bar and the attendant hazards shoreside north of there. While Grey's Harbor is picturesque, don't plan on it as an escape hatch
in bad weather
, particularly at night unless you don't have someone aboard with local knowledge of the harbor and its' approaches.
Give Flattery a wide berth as well as sea conditions can be problematic anytime of year.
An experienced commercial
fisherman would make an excellent crew/skipper for the passage
provided he has spent time fishing
I'm surprised at the cost you were quoted for trucking your boat north. If you help out with the derigging and prep work, to get her over land from Portland
to Olympia, WA, it shouldn't cost that much I wouldn't think and there are easy out/easy in yards in both locations. Mileage isn't all that great either.
If I were still in the business, I'd do the trip in a heartbeat but unfortunately considerable past that now, healthwise... good luck, Steve... cheers, Phil