When practicing Hang up And Try Again, the most important rule is to be polite and concise.
Usually better not to waste 30 minutes trying to convince someone that a rule exists when the next agent will know it immediately (and when the initial agent's supervisor will happily back them up, compounding the problems). Also best to make as little of an impression as possible so you don't end up with an inaccurate annotation on your record.
Most tricky operations have some kind of HATA Constant (the number of times you times you need to hang up and try again). It would be interesting to hear what that number is for waitlisting awards.