On the difficulties of planning how to cross the Prairies on a bike

The Prairies: flat, with roads everywhere. It should be easy to plot a route from Calgary to Winnipeg taking in the interesting bits, right?

Wrong. The thing is that there are almost too many roads, especially compared to the number of settlements with accommodations. Furthermore, my tastes don't necessarily coincide with a logical, efficient route. I mean, wanting to go through Vulcan, Alberta as well as a portion of Canada that drains into the Missouri and go to Moose Jaw and Grasslands National Park, whilst getting to Winnipeg in time to fly back to Montreal for a friend's wedding is probably a bit much, especially as the road system is essentially aligned with the cardinal directions, and I wish to go at "funny angles", this adds a lot of "unnecessary" kilometers. Nor does it help that I haven't quite got to the two-wheeled gypsy mode of cycle-touring. As well, it is surprisingly difficult to figure out which bits of roads in Saskatchewan are paved or not. To top it off, the only cities that are roughly on my route that aren't end points, are Moose Jaw and Regina which are only a day apart! I am actually toying with the idea of skipping Regina in favour of Moose Jaw in order to save a day. Probably a bad idea, but it would let me go through McTaggart, Saskatchewan.

Anyway, I still have more than a month to work out a least a tentative route, one which allows modification according to the wind and weather, as in theory, if I caught a good tailwind, I could do 200 km in a day, but I would be unwise to plan such a day.