Someone on another forum was talking about just purchasing an iPhone 3G from Rogers then jailbreaking it. I thought I'd post my reply to them, as others on here may be thinking the same (I'm not trying to be big-headed here, just trying to be helpful)
The other factor here is that you will not be able to purchase an iPhone 3G without also signing a contract with Rogers. You cannot, as you could with the 1st gen, purchase it, walk out the store, jailbreak it and use it with another carrier.
Again some math...
$337.87 - 16GB iPhone 3G including taxes*
$76.22 - One month's worth of contract, even if you don't use the phone**
$100.00 - Min Early Cancellation Fee (not including tax, unsure if it does or not)
$514.09 - Total price for obtaining the 16GB iPhone 3G and freeing it from Rogers.
*This is the rumored subsidized price. It's possible they may offer PAYG, or an unsubsidized phone for a higher price, so the total cost would be even more.
**I recall seeing something about AT&T requiring you to return the phone to them if you cancel within 30 days, thus preventing people just buying the phone and canceling on the spot to jailbreak it. I would fully expect the same to be true with Rogers. If not then I'd expect you to be hit up with the max $400 Early Cancellation Fee.
There is another factor here and that is that the iPhone 2.0 firmware is not final yet, and the phones are not out, so it is still unknown wether they can be jailbroken. I'm sure a lot of effort will be put into it, as with the 1st gen iPhone, however, it could take time. Also, even if you did jailbreak it, who are you going to use as a carrier? Do any other Carriers provide high-speed 3G GSM services in Canada?