I used to try to be empathetic, but then I realized I’m just taking up even more of their time. The best strategy imo is to just get to the point as quickly as possible so both you and the rep can get on with things.
However, if the call is going to be long regardless, I do banter a bit.
The closest I had to that job was as an IT help desk person at a university working with faculty. I only had to actually interact with 3-4 people in a given day, so I don’t know if it really counts.