Islander 36? Nice enough boat, kinda low in tonnage but for short small hauls should do pretty well. Dunno as if you could make the boat payments hauling small lots like that, though.
Sailing inland waterways, too, with ripping tide currents up there. If you picked the tide right, half the work would be done by the current instead of the sail. Nice scenery, really COLD water, great food when you get to port and lots of nice little ports to poke about in. We sailed a friend's schooner up that way for a couple of weeks. Had he not been on some sort of a weird macrobiotic diet (and insisting the crew do the same, too, arrgh!) it would have been a wondrous time. As it was, we were fishing and clamming because we wanted something to eat other than brown rice and Dr. Bronner's whatever sauce. We pulled into Bremerton and the boat upwind of the slip was frying bacon. They never knew how close they came to being boarded with pirates making off with their breakfast. We stormed the local diner in town instead.
Pike's Place Market, where the video started at, is a hoot, if you buy a fish from the folks in the center corner place, they grab it up off the ice bed and toss it back to someone else to wrap up. Then it comes flying back wrapped. Dunno if they ever drop them or not.
There used to be a bigger sized sailing freighter which went out of the Kona side. She was wooden and went down about a decade ago, I think it was. Hmm, guess it was longer ago than that, make it almost two decades ago. She went through the South Pacific Islands taking freight to the smaller ones which don't have much freight service.