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You should develop quickly. I mean, quickly. By 1600 you should have:

  • A population of 50-75, half of them specialists working in their industry, definitely more population than all 3 (or 2) other powers combined
  • An average support of 25%-50%: remember to get Bolivar as soon as possible after 1600 to get 20% for free
  • Overproduction of lumber, ore, hammers, tools, food and horses for your needs and for development, done mainly by specialists
  • A decent production of at least one cash crop (and not boycotted)
  • A fleet of at least 2 Privateers, and at least 3 Merchantmen/Galleons
  • At least 5 wagon trains
  • At least 50 horses in (almost) every colony
  • Roads and plowed fields on almost all used squares and roads connecting most of your colonies
  • Lumber mills and warehouses in most colonies
  • A few printing presses, docks, schoolhouses, blacksmith's shops, stables, maybe also newspapers, warehouse extensions, and other shops

If you miss one or two spots on this list, it's all fine; not everything works the same every time. If you're way behind this schedule (for example with only 30 colonists, or without any tool production), you're playing too defensively.

You can win the game, even win with a good score, with far less fighting spirit than necessary for such development speed, but why settle for less than you have to? ;-)