IF you want to charter the boat, the best way is to put it into one of the charter companies--several in Anacortes. They take a fairly high % of the charter, and you do not have as much election as to when you can use the boat, but they maintain the boat, provide moorage, check out, advertising, insurance etc.
I have both done individual charters and long term leases of boats and RV's I have owned. Generally it is an exercise in frustration. Insurance is a real issue--which you must have to protect the boat, you and the charterer. In my experience the wear and tear on the boat is more than it is worth. I see my boat as a very personal posession. Even loaning it to good friends who are very skilled, I find that it is dinged up and not cared for the way I would care for it.
There can be tax write offs (see your accountant), but again, for a C Dory I doubt that it is worth it. Many of the larger vessels are in full time charter programs and they may be successful, but often come with a skipper and crew, who care for the boat, and guests.