Jake, my personal view is that I look to Disney first for my cues as to new content.
From the Developer's Diary #13, 1/27/09:
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Take for example the Kraken , maybe you've heard of this mythical sea monster? As the right-hand squid for Davy Jones, we can officially say the Kraken is coming to the Caribbean this year. As soon as the development team can wrangle him with their fishing nets they will release him with specific orders.
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And from the Developer's Diary #14, 4/17/09:
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The Kraken. This beast has proved to be a real challenge. Why? Well, it is basically our next story chapter, many things will be tied to it, such as Notoriety increases, new Story Quests, and so much more.
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So from these two Disney announcements, early this year, we were led to believe that the Kraken is our next story chapter, that it's linked to Davy Jones (not Jolly Roger) and that we would see it in game before the end of the year.
That's the new content I've been looking for. We've seen new story quests and Notoriety increases, but as there's only 17 days left in the year, and the Kraken hasn't shown a tentacle on test yet, I'm not hopeful that the new content I've been looking for will appear on the horizon before 2010.