For what it's worth!
My '07 K9 picked me, didn't get any miles on 'til after I bought it, but it just felt "right" from the first sitting, and I've never looked back. I'm a small fry puss at only 6-3, but did put on extented controls. I'm also a newbie with only ~3700 miles, but ~400 mile daze are light work on this scooter. The more I ride it, the better it gets!
Comfortable load on Alaskan roads...
Keep the 'Glide!! Hard to put that gear on a Dog when traveling and not look like a rat bike. Do you pack a significant other? I've got a few years and a lot more miles on Harleys, and will never part with my '02 softail. When I have to ride in shitty conditions, I'll always take the Harley if I have a choice. But having done the Dog in "as bad as it can get" conditions, it's easier to clean up afterwards...
Whatever, do it man, and stay tuned to the forum - best bunch on the planet.