We're combining a lot of elements here. Let's go one by one as to the factors.
1. Inexperienced owner and boat new to him. Well, the inexperienced owner part can be overcome with an experienced captain. As to the boat, I'd want a shakedown cruise or two. I'd cruise to Astoria and then go outside and run it a while if it handled that ok. Back to Astoria. Repeat if necessary. Then consider the trip.
2. Cruising the coast. There are many ways to do that. Yes, you can go 100 miles offshore and do it 24/7 and ignore all conditions, never paying attention to the weather. You can be as irresponsible as you want to be. However, you can plan carefully and take extra precaution. Most of the trip you can find a marina for night. The one night or so you can't, you can find a decent anchorage. You can sit as long as needed along the way. The stories of storms coming up out of nowhere is a time without all the forecasting and tracking we have today. They can still sometimes come up quickly, but getting caught out in one really shouldn't happen on a trip this short. For extra precaution you stay in if at all concerned. If a storm is forecast for tomorrow but predicted to be relatively mild, perhaps you stay in anyway, just in case it's greater than predicted.
3. Cost and convenience. There it's how you want to spend your money. Not a lot of difference in cost of transporting by land vs. water when all is added up. I'd rather spend my money boating. You might rather spend it shipping.
For those of us use to seeing one town run into the next and development all along the route, the beauty of the coast is magnificent. I don't think it's possible to perceive it from land as you can from the water. So natural and so relatively untouched. Miles and miles of nothing. May seem boring to some, but beautiful to us. And the sea full of so much to observe.
In 2014, we made many trips up and down that coastal area. Conditions varied widely. We had 10' swells that were amazingly calm with 13 second periods and we saw 4-6' wind waves that kept everyone in port. In addition to all the weather information available, the Coast Guard gives great information on conditions, especially of every bar.
If you show the sea proper respect, you won't need to fear it. While I wouldn't advise an inexperienced boater to head out on his own up the coast in a boat he just got and doesn't really know, I certainly wouldn't advise people that the area along there is so treacherous no one should ever transit it. The truth is in between. Then it comes down to a personal choice.
This isn't a trip to be taken lightly, but it's also not Cape Horn.