Absolutely, I wouldn't even consider this if the segments were on the same airline (e.g. KL-KL), or even two different carriers on Amadeus (even though they're in different alliances, for example, I would be pretty certain this wouldn't work between AC and KL, for example).

There's no good or service in the entire world whose pricing is as complicated as airline tickets, especially international ones. Airlines have created a ludicrously elaborate system of rules and systems to try to extract as much value out of each customer as possible, and many of their practices have been described as dishonest, deceptive, misleading, etc. Those Byzantine rules sometimes create opportunities for customers though. Is it dishonest to purchase what you know to be a mistake fare? Is conventional hidden-city ticketing dishonest? Different people will have different views on those things.

In this case, if there a way for my idea to be successful, everyone would be better off. I wouldn't waste a big chunk of my day needlessly flying back and forth and could refund my positioning flight, and WS wouldn't have to expend the fuel flying me from YVR to YYC, or could sell my seat or charge somebody a fee to same-day change or upgrade in to it. I would also save KL the money they'd pay to Aspire, since I wouldn't bother to visit the lounge at YYC if I was just coming from home.

Yes, KLM would have wanted to charge me a couple thousand dollars extra to originate in YYC before I bought the ticket, but now that they've sold me the ticket and the flight is getting nearer, their profits would actually be higher if they let me do what I would like to do.

Now, that's not how air ticket pricing works, I wouldn't be complying with the contract that I made in purchasing the flights, yadda yadda yadda, but is it really "dishonest" to do something that actually benefits all parties involved?

Purchasing a ticket that requires positioning is already a way of gaming the system. Why not find out whether the system can be further gamed to extract more value?

As I've stated multiple times, I have booked the positioning flight, and I'm prepared to take it if need be. But if I can avoid the backtracking, I will. As for not trying to "wriggle out" of an inconvenient segment, why on Earth not? My original hope when purchasing this ticket was that booking a connection right on MCT would give me an opportunity to switch to something more palatable (e.g. still position to YVR, but take YVR-AMS or YVR-CDG instead, or delete the YVR-YYC segment, or whatever I might have been able to do). Despite all the massive changes to airlines' schedules over the past few months, both of these flights have stayed stubbornly at their original times, and are unlikely to change at this point. Was that "dishonest" of me? Definitely not, as far as I'm concerned. I gambled and lost on that point. But I was willing to take that risk.

The bottom line is the airline industry is heavily stacked against consumers. Airlines charge whatever they think they can on any given route, whether it has any relation to what it costs them to operate or not. They say "schedule not guaranteed" and then cancel or massively change the times of your flights, even though they've already taken your money. They might have to give you a refund, but you might be forced to make an unpalatable choice between paying a lot more for a new ticket from someone else, or accepting an itinerary that's far worse, from your perspective, than the alternatives you could have booked when you bought the ticket from the first airline.

If the consumer can occasionally find loopholes or inefficiencies that work in his favour, I'm all for it. Airlines live by the sword, they can die by the sword too.