My wife, and I consider Sitka our home town. We are coincidentally leaving Washington State tomorrow, and slowly making our way to Sitka. We expect to arrive mid to late June. If you do manage to find a charter opportunity feel free to get in touch.
Glad that you mentioned Fisheries Supply. Fisheries staring business in 1928, and is still owned, and operated by the same family. They are into the third generation, and have always offered outstanding customer service.
From reading these posts, it seems like this is what most of us are looking...
I think trailing to Prince Rupert would be my choice. I have lived on all three of the islands in question, and as others have suggested, your boat is perfectly acceptable for cruising that area.
Funny you should post this story. We didn't see the accident, but the red bottom paint scuff on the log lasted quite awhile. This was literally in our friends front yard.... lol.