Never been to a tailor at Sears before, but removing pleats from pants is a pretty heavy-duty job - especially if there is a pattern to deal with. I can't help you with a tailor in Calgary, but you have the right idea looking for quality over cheap/fast. If the guy is skilled, it'll be worth the hundred bucks or whatever. Especially for an Oxxford suit, which is a thing of beauty.
Next time, just say NO to pleats.
