We are booked for July 27th for early start and pushing off the morning of the 28th between 9 and 10 on the 514PC. We chartered this 2 years ago and it is a beautiful boat and wonderful to command. As stated slow is pro. They now have a Captain go out with you if its your first time chartering the 514PC. It is no big deal, just an on the water check ride. You were on the 433 and said you had no problems. You will do the same with this boat. Handles like a dream and plenty of power to turn or spin the boat with the throttles. Dont stress over it and get some good tips from the Captain. Remember its free so a nice free personal private boating class. You only have to do it this one time. This is new this year and I think its because of past charters or and insurance requirement. As far as Chartering the 3-5 yr old is smart thing to do. We are doing the same and will contact 2 weeks prior to our charter for a free upgrade to a newer boat under the Captains Reward Program. If you have not signed up (Maybe automatic enrollment) contact them to check. You just have to had chartered with them in the past 5 years to be eligible. It also comes with a bunch of discounts at places around the islands. Do this now though so they can send you your Captain's Card to use while down there. I remember it took a little bit for them to send it to me. What dates are you looking at going? We picked the 28th because there is a big price drop starting that week. We usually charter at the end of May but had to push back to end of July due to schedules.