This is one of those events that will likely be similar herding cats. There are so many aspects to consider. When I made my trip to Whidbey Island, WA last summer, All I had to be concerned with was getting to the island by Sunday night. After that, the pace for the rest of the trip was dictated by my butt and the amount of daylight remaining.
The first few days of this trip is similar in that riding up through the Unites States should be a snap. The ride through Canada entering from northern Montana up to Alaska is about 2,300 miles. Google Earth shows some pretty decent roads all the way up to to the Alaska border. As I learned riding through Idaho, construction could certainly impact that.
I'll need to look for places to sleep, be they hotels, camp sites, abandoned gas stations, whatever. I don't plan on carrying much in terms of camping provisions and I'm spoiled, so hotels and cabins are my plan.
I'll need Canadian currency, which should be no big deal.
I need to look into the Canadian laws regarding carrying my pistol through Canada. Alaska is a self-protection friendly state, so it's no big deal once I re-enter the US. There are Canadian forms and fees that make it possible, but generally speaking the Canadian government prefers unarmed peasants. I just need to decide if it's worth the hassle. When I think of the bears up there, the hassle seems to diminish.
June is nine months away, but I laid awake for hours last night mulling all this over. I'm generally not one to over think things. I just hate to miss important details. That said, I suspect there will be plenty more of those nights. I ordered the 2010 edition of The Milepost to help with initial planning and to make for some good bathroom reading. The 2011 edition will be published next March. I'm sure I'll buy that one too. I still have 2006 and 2007 editions laying around. As I mentioned, Alaska has been calling for a long time.