With the highest data plan that Rogers offers being around $200 for half a gigabyte of data, it doesn't look promising.
Rogers will need to lower data prices at an extreme rate to get the iPhone, but it won't happen, since there's a 3 way monopoly between Rogers/Fido, Telus and Bell, they're taking their time with everything. I've seen prices go up rather than down. I remember 4 years ago I could get an excellent voice plan for 20 bucks and options for pretty cheap, but due to the monopoly structure.. the plan I had 4 years ago is now worth 2x more if I was to get it as a new customer now.
Fido had an unlimited data plan for $20 before it was purchased by Fido, then again look at their original foot print, it was exclusively in urban areas with hundreds of thousands of people.
Rogers has a large infrastructure to look after, many times in areas where there's only a few dozen customers within the radius of the tower. With that being said, there is the SAF, and rival carriers are able to offer cheaper data at the same time while at times having coverage in much more remote areas with much fewer people than Rogers does. CDMA carrier MTS has a half gigabyte option for under $100, which is half the price of Rogers.
Comparing phones, Rogers now sells the TyTN by HTC, with a $60+ voice and data plan (I think) it costs $400 with a new account with Rogers, while for the same phone on AT&T it's $100 less, plus Rogers requires a 3 year contract with it, for a 2 year on Rogers it's $600.. yikes.