The Great Divide

I'm not sure how the idea of riding the Great Divide, a 2500-mile, mostly off-road, bike route from Canada to Mexico along the Continental Divide, came about. Were Steevo and I joking about it in chat? He had mentioned it and I have had it in the back of my mind since I first heard about it years ago. Seemed like a great way to see states like Montana and Wyoming and really appreciate some parts of this huge country that most people will never see. Next thing I know I am ordering the maps........
This route is extremely remote, some people carry satellite phones and the route creators, Adventure Cycling, recommend no fewer than three people. The weather is also extremely variable. These two issues = more gear. More gear = more weight and a tougher time getting up hills. This guy claims 191,000 feet of elevation gain. But there is a race and the winners do it in as few as 14 days. We have about 30 days because I am teaching till the end of August and have to be back in late September for some classes I am taking. Is that enough time? We plan on using cyclo-cross bikes as these will be much faster and the route is not too technical. Steevo is a cat-2 road racer and a cat-1 cyclo-cross racer, which is good, but makes me nervous. Him and I rode cross country the same summer, as our first bike tour, but we rode the opposite way (him with a group east to west, myself alone west to east). We both have touring experience, both have bike handling skills and both are strong riders. This trip is more like a backpacking trip because of the remoteness and all the time in the mountains (read: unpredictable weather), but we both have some experience there to.