Call me fussy, but unless you are going to include dish soap, I wouldn't want to use the same cup all day, let alone all week. We just sat at the swim up bar and kept the bartenders busy. If you're drinking that much, you'll be done them before they have a chance to melt. For the room keys, we provided everyone with a waterproof card holder that had enough space for a little bit of tip money. I'm not sure if everyone used what was in their OOT bags, but I like to think that they were useful. It was definitely beneficial to use a cotton bag that could be reused throughout the trip and was brightly colored so we could spot our guests spots.