WOW ! ! ! congratulations on planning this undertaking! I have never come close to even considering a trip like that but I would like to offer my advice.
I am originally from Saskatchewan. I know wind. The weather today is described as "partly cloudy and breezy" "Breezy" is NW winds sustained at 23 mph w/ 37mph gusts
Since last night the wind was up to sustained 36 mph w/ gusts up to 46 mph.
The prevailing winds are from the west so I would strongly advise a West to east route or you will be cursing the prairies. There is NOTHING to block the wind and it never ends. As experienced cross country riders have said "When you climb a mountain pass you know you will eventually come to the top and get to come back down, but wind never ends"
Your prairie ride will cover over 1/2 of Alberta, all of Saskatchewan and most of Manitoba - trust me you don't want to be bucking the wind all the way.
If I remember correctly all of Hwy #1 is 4 lane now in Saskatchewan. If anyone recommends Hwy #13 really check it out. It has VERY low traffic but spots are under construction - if you choose to do #13 let me know - my sister lives on it and so do my parents. I bet they would put you up for the night! My aunt lives on #1 and would do the same
Good luck and keep us posted!