I find "label created" statuses to be pretty annoying. They seem to really mess things up when it comes to tracking items.
I used to be pretty obsessive about tracking my items until I realized that all tracking tells me is where my item has been, not where it is, and the most important thing I should be concerned about is whether I get my item within the estimated time in the listing and condition promised by the seller. Knowing where it is or was between the seller and myself doesn't really do me a lot of good.
I think there's a pretty good chance that your item is on the move but for whatever reason, the scan information isn't being transmitted to Canada Post's database. Again, having the tracking number created well in advance seems to mess things up there for reasons unknown to me.
As you say, you need to wait until the last possible estimated delivery date has passed before making a claim of item-not-received.
