As per the earlier comments, it's not that bad a deal if you're buying it purely for YYC - YYZ. For the other destinations, I think it's probably much smarter to buy the Latitude Pass for the West. If there was a YYZ-YVR pass for the same price as the Calgary pass, I'd buy it in a heartbeat, since I'm going to be doing that route all the time pretty soon. That said, the upgrade situation seems a little mean -- only being able to upgrade one day in advance rather than four days for an Elite (like me) with a latitude fare or seven days for a Super Elite (which I will almost certainly be next year).
Also, I've been told by several check-in and gate agents that it's not permitted to use certs to upgrade flights booked with a pass. Are they misinformed? They have let me do it, but I've been told I'm technically breaking the rules.