A good way to start is to look at the fare rules, which will normally tell you where you can have free connections / stopovers. Then just use the multi-stops option on Expedia, Destina etc., and enter as many stops as needed. For instance, for a YOW-YYJ trip, I searched for YOW-YWG-YYC-YYJ instead to maximize the number of segments. This way I managed to get YOW-YYZ-YWG-YQR-YYC-YVR-YYJ for the same fare as YOW-YVR-YYJ (12 segments instead of 4). You will have to spend some time playing with all the options, but it shouldn't be too difficult if you keep the fare rules in mind.
[This message has been edited by Szut (edited 09-08-2002).]