Kind of. I wanted him to be a captain, but not be the sole pony in charge, hence why he sails under his father's colors as part of his fleet. I also wanted to show that since he's still a young stallion, he's prone to overconfidence and mistakes, and the perfect thing was getting the ship stuck somehow. After that I just had to figure out how he'd get in that situation, and I figured it would happen on his first real mission. For that I just kinda looked at the map and went "Okay, if I was a pirate, where would I raid? An Equestrian city? Possible, but along the coast there's rarely ever something aside from the navy that would impede me, so that's out since I don't want the ship sunk. So what targets would both be rich, possibly get the ship stuck, and not really be cared about that much? Hmmmm... well, sandbars are common in rivers, so something inland along a river. That could get the ship stuck. But what- WAIT! Nobody would care about the Diamond Dogs. They're jerks, and they have tons of gems!" From there I just planned out the larger attack along the three rivers headed toward the lakes, and gave him what should have been the "shortest and safest" route. Basically... I pulled a Gilligan's Island and gave him a "three hour tour". xD