Well here's an idea. Merchant Voyages kind of suck, and they're a chore. But if you do other voyages, all your reps level faster than Merchant so you're stuck doing Merchant at the end. So maybe server hopping is the most fun way to get pirate legend because you can grind all your factions at the same time and get some PvP in without having to chase people down. But really if you can get a skull fort every hour, I don't see how grinding a different way is faster when you consider you're leveling 3 things at once.