To add to the above comments your day 1 is a bit ambitious. You probably have less than a 50-50 shot at winning the boatyball lottery for Cooper in June on a Saturday. If you do win I would head over to Peter at Deadman’s bay for a lunch stop then up to Cooper if off the dock by 11. If you get off the dock late I would just go straight to Cooper. If you don’t get a reserved ball at Cooper I would consider just going to the Bight. You can hit the Indians as you approach if a ball is available. From there grab a ball and dinghy to the caves. Try the Boatyball lottery again and if you win head up at your leisure. If you lose head up early to get a FCFS ball. It’s a great place to hang out for an entire day.
As far as the paddle board they take up no space and are no issue to have onboard. They are not rented locally at most places so if you want one just have the Moorings put it on.