By now you should have more captives, so put your surplus ones to good use.  Build a second sawmill and a timber camp near it.  Also, build another cornfield or two as you'll need them to supply all the new mouths on the island, as well as your sea rations factory.  Check their resignation level and add order and fear decorations if needed.

Now you are ready to turn your attention to keeping your pirates happy.  The first step is to build a brewery and place it near your cornfields.  Next build some first level entertainment: a dive, masseuse, and an animal pit.  There's no point in adding higher level entertainment as you probably don't have enough high level pirates yet.  Use your Island Log to keep an eye on your pirate ranks.  As you get more higher level pirates, start by building more first level entertainment and setting the service quality to the next level on some of them.  Leave their rates at bargain levels to keep your pirates happy.  Once you have several ships and they are spending most of their time plundering, you can raise the rates as your pirates will be richer and more willing to pay high prices.

Now for the most important rule of pirate urban planning: keep your entertainment away from your industry.  Pirate structures create anarchy which is bad for captives, and captive structures create order which is bad for pirates.  A well-designed pirate town has a section for industry full of gallows and skeletons that oozes fear and order, and a pirate entertainment district that is filled with security and anarchy.  In addition, the pirate section should always be close to the docks.  Don't make them become disgruntled by forcing them to walk through a well-ordered section of town just to get a pint after a hard cruise.  When you reach the point where you have plenty of surplus lumber, add pirate housing near the entertainment structures to allow your pirates to rest and stash their wealth.  Again, keep the housing close to the docks and away from the captives.

At this point in the game you should have a healthy economy going, so you can afford to add another ship or two.  Don't assign one ship to capturing more laborers and craftsmen and the other to cruising.  Mix the missions up so that the crews of both ships get the chance to advance in rank and become wealthy.  Monitor your pirates so that you have entertainment structures available to all ranks.  If you have only a couple of high ranking pirates and they become disgruntled, it can be cheaper for you to assassinate them than to build a set of entertainment structures to keep a couple of pirates happy.  Make sure you don't knock off your ship captains unless you really want to, though. 

Your pirate island should now be well on its way to success.  Your healthy economy will serve you well as a basis for building the higher level structures ... and for making your stash grow ever larger.

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