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Before Tradewinds: Legends, there was Tradewinds 2, set in the 1700's Caribbean. The look of this earlier game is similar in that the characters are cartoon-like, but overall the art is less colourful, lending it an older look.
Even so, the random character generator is just as good, and can provide a ready source of characters of different nationalities. Combined with the nationalities presented in Tradewinds: Legends, you've practically got the whole world covered.
Although the setting is the 1700's, this period is still old enough that it can squeak by into "generic fantasy", which tends to be around 1500's earth and earlier (plate armour not yet phased out).
Many of the same comments made about Tradewinds: Legends apply here: The potentially endless combinations, the same-ness that comes after seeing hundred of images, and the subjectivity that colours whether you feel the generator is reliable...
So, before you think about getting your own copy, please tour and make use of our gallery, try the demo, and consider the pros and cons before making a final decision on whether you should purchase Tradewinds 2 as an art and portrait resource.