I have lots of conflicting emotions about this chat log. Here are a few of them, and some additional notes:

• Fate would have it that the person assisting me had an obviously Indian name, thus dredging up all the stereotypes about outsourcing, and about the Indian culture of always say "yes" and agreeing even if you don't understand.
• I realized after re-reading the logs that he had meant to type "complete address with postal code", but wrote "complete with postal code", and so I thought he was just asking me for my postal code. So when he started demanding more information from me, it probably felt more onerous than if he had just directly asked for my full address from the start (which is what he had intended to do).
• To be honest, I became a bit paranoid when (I had the perception that) he asked for gradually more and more info. I glanced at the address bar of my browser, and I noticed that this support line wasn't part of the bell.ca domain. There was the tiniest chance that this was a man-in-the-middle hacking attempt, though much more likely it was just the domain of the company that was being outsourced to provide support. The guy convinced me he was legit when he started citing all my account info back to me.
• On the one hand, it looks like being a little belligerent can get you past obstacles in customer service, including security systems. I guess that's one of the first lessons in social engineering hacking.
• Halfway through, I got tired of the long delay between his replies, and so, yes, I manually typed in the timestamps.
• When I started doing that, the guy suddenly became a lot more helpful. Coincidence, or spurred by nervousness?
• Another possibility is he called his supervisor, and his supervisor started typing in this stead. The change in tone of the conversation is pretty dramatic, so I think this theory is plausible too.