kokopelliTim: I like your thinking. If you wish comfort and spend most of your time at a dock, why not go for comfort? I know lots of sailors go for that blue water boat and seldom raise the sails.
For me, finding a boat that I could see out of while at anchor was a high priority. I don't do caves! Still, I sometimes wish that back then I'd been more open to houseboats. That single level has a definite appeal especially when it rains.
I've had three knee surgeries, so along with my ribs have my own personal weather forecast mechanisms.
Boat hulls are a preference (over pontoons) and I am NOT A FAN of inboard-outboards There are seals that leak (they all will deteriorate) so pick and outboard OR an inboard engine.