I'm hardly one to give you advice, but I will anyway - at least a little.
Your basic strategy sounds okay - consolidating the island. Based on your description of the second game, perhaps you should seek some allies or trading partners on the mainland. That way when you inevitably are in conflict with your neighbors*, you don't take such a big trade hit to the economy.
But you are right, TWS2 definitely stepped up the challenge - at least initially. Oh how I remember the wailing and gnashing of teeth from most all the players as the game handed them their heads. That eventually changed over the course of time.
* See below
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