rsn48: I am somewhat familiar with both the San Juan and Gulf islands and I like what I have seen of them.
Part of my motivation for getting a boat that can go a lot further than the average runabout is that I want to explore the entire inside passage, with a primary goal of finding a water access property where I would like to live year round. In general I'd like a little more remote. But I'm not crazy about off grid.
Looking and reading online is fine, but nothing beats seeing the place in person, and getting to know the entire area.
Being retired, I have plenty of time to explore and I plan to extend the season as long as is possible. I was boating in January in Ontario this year, pushing through some broken up ice.
Not having to deal with ice from January to the end of April sounds like a dream to me. And a boat with a closed cabin and a heater? Luxury.
I'm hoping I can avoid most of the crowds by being away from the popular areas in high season. Desolation Sound and the Broughtons sound ideal.
Since I am trying to find a warmer climate, not a colder one, I imagine I will want to live somewhere well South of Alaska. If that means I have to put up with more traffic, so be it, it can't possibly be busier than the lake I just left (I hope).
As for a bigger boat, of course I'd be more comfortable in a 34, 37 or 42 foot boat. But I can't afford one. And I don't want to get an older one that requires maintenance or is beyond the engine warranty. I want to be on the water, not sitting in my condo waiting for the boat to get out of the shop.
As I said, I am well aware the R27 is not the perfect boat, but it suits me. I am still considering one other used boat that is somewhat bigger, but I am very reluctant to pursue it due to its significantly higher cost and likely maintenance that I am not capable of doing myself.