Use ITA matrix.

In the advanced field, drop in the following line:
ac+ / f bc=g|bc=v|bc=u|bc=w|bc=h|bc=u|bc=q|bc=m

This tells it to look for one or more AC flights in the fare buckets listed (which result in flex for your route).

That gave me: YOW-YWG-YYC-YEG-YVR (flights 8525, 8335, 8142, 245).
For $488. Departure at 8.20 AM, arrival 4.09PM.

Then start pushing it. Replace "ac+" with "ac ac ac ac ac" which means you want 5 flights on AC between origin and destination.

What about YOW-YYZ-YWG-YYC-YEG-YVR for $492. (AC 441, 261, 8337, 8164, 225)
Departure 8.07AM, arrival 10.02 PM.

I think 5 flights will be your max, although someone would have to verify the routing rules on KVS or expertflyer to double check. You could leave earlier and maybe squeeze in another flight if routing rules allow.

Note: I only checked June 5. June 6 should work too, but looks a couple of dollars more expensive. Have fun!