I am a truck driver that lives in Canada (Saskatchewan specifically) and I will be starting to do some Canada/USA work in the near future. My current phone service provider doesn't have very good plans for North America calling and as I like to phone home at least once a day, this will end up getting kind of pricey. I am using my phone for about 2,000 minutes every month as I also use it to contact my dispatcher and...well...anyone I would contact with a phone while I'm out on the road I guess.

Does anyone know of a good service provider that would let me pay a flat rate for a bundle of North America minutes every month? It doesn't matter if this is an American or a Canadian provider, it just needs to be able to send me my bills in Canada which is something most any of them can do I presume.

NO USA carrier will bill a Canadian address unless you billed it to a credit card. Telus would be a good choice if they are available in your home area since they are powered by Verizon Wireless in the USA and their own network in canada. They have extensive North American plans.
http://www.telusmobility.com/bc/plans/pcs/family.shtml?code=11