I would have made just such a comment, and I know several AC staff who would make just such a comment. It is just these people with whom I have struck up a rapport in the few minutes of checking in my luggage and managed to get an upgrade in return for a few minutes of levity.
I was checking in for a flight from YEG to YYZ -- gave my Aeroplan information to the ticket agent and joked that I would love an upgrade, just like the one's claimed by the passengers ahead of me. She could see my travel history right there and see that I had 9000 Aeroplan miles and joked that I would need a lot more to get anything like that. We bantered back and forth for a few minutes with comments like "You do not have even enough to get a cup of coffee."
Someone else might have taken those comments as rude. I laughed, the agent laughed and we went our separate ways -- me with my coach class boarding pass and a smile.
I never did see that agent again, however her co-workers at the flight gate obviously knew who I was when I tried to check in for the flight. They requested my boarding pass and took great joy in ripping it up in front of my eyes and those of every other passenger on that 767 out of Edmonton that night. In its place I was given boarding passes for Executive First seats for myself and my fiancee. With nearly fully reclining seats with leg rests, double mixed drinks served just before take-off in both Edmonton and Calgary, gourmet meals, and champagne & orange juice served in the morning, there just wasn't much better happening on this particular red-eye flight into Toronto.
Their job is stressful enough as it is -- and I think everyone knows that no airline charges anything to print a boarding pass. Give the AC staff a break and enjoy the fun with them.