The liveaboard idea was a fleeting thought that I quickly abandoned. All the advice and ideas here have helped me narrow things down.
I would hope that a brand new R27 with a Yamaha outboard that has a 5 year warranty would not be a problem maintenance wise. I can certainly do oil changes and things like that, although I would probably let the pros do even that as those costs are not prohibitive.
I'm expecting my major issues will be with electrical/electronics, and I just hope the major items are reliable.
I could afford a 31 or 34 foot diesel Tug that is 5 to 10 years old, but I can't imagine they will be less maintenance than a brand new outboard.
If I get into nasty weather I believe the advantage of the R27 is a speed that would get me out of the way before it hits, hopefully. I have all the time in the world and I would happily wait for days to get better weather.
I'm really interested to learn more about the weather year 'round. My first year I will be quite cautious of course. As long as there is not 3 feet of ice, it'll be an improvement over what I am leaving.