Please know, the "oldies" on this site can only advise based on what happened on "our" year. The info you posted is not the same as what we were required to do. I would call WP for clarification. They really are there to help and do not want miscommunication or confusion. They will not bite, nor will they recind an appointment if they are asked a "dumb" question.
A little extra info on the shoes: you are not breaking in the shoes as much as you are breaking in your feet. Most students wear tennis shoes, flip flops, and other soft-soled shoes. They do not often wear dress shoes. This is to get your feet used to something different. You will spend a good amount of time in these shoes the first few days at WP...so you want to minimize discomfort. My son wore his to school one day (that was all he'd do!), around the block a few times, to all the WP functions (senator reception, governor reception), and all the graduation functions. Maybe he had them on a total of 15-20 hours before R day, and he was fine.