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You folks live in boating paradise.
I spent a week up in the San Juan's this past September and really enjoyed cruising around in my friends Outrage 18'. I could see that there were many other fine boats more suited to staying overnight in than even my Outrage 22' Cuddy. So, that is one of the reasons I sold the Cuddy.
Here is a small movie of the San Juan Island trip:
San Juan Island Trip

I also agree that one boat may not satisfy all the needs a person has. That's just the way it is.