Monsieur - -
The physical part is the easiest part.
It's the mental part which is far more difficult.
Yes, you will have many days of headwinds in the Prairies.
On circle rides, you only go against the wind for about half the ride,
When you ride cross-continent you may have day after day of headwind.
It sounds as though you are going solo. Have you been alone that long before?
Ipods are nice, but there's no substitute for the real thing.
Eating at a cafe is a way to have contact with others - even if it's a Tim Hortons.
Then there's the weather.
I certainly hope you are Canadian because starting in Newfoundland in the spring can be damn cold.
Spring also tends to be the wettest season. Got good raingear?
Are you allowing yourself leeway so that you can wait out a bad spell?
I repeat - the hardest part is the mental part.
Good Luck - -
J