Also, don't forget that you'll have support options if you need them-- just take a
VHF. Here's a photo gallery of a trip from Port Townsend to Portland, and you'll note that they ran out of
fuel in the mouth of the Columbia and had to be towed to Astoria by the Coast Guard:
http://spunt.aigc.net/gallery/album98
My preference would be to avoid that, but it's good to know help is around. This gallery is from a good site about sailing in the area:
http://www.sailestrella.com/
You may also want to join the Cascadia email list (regional sailors). In just the last few days, there's been several posts about crossing the bar from experienced sailors:
http://www.sailcascadia.org/
Good luck!
Jim H