A stiffer fin creates a bit more lift and thus is better in lighter winds.
My understanding is a bit limited and is wavesailing oriented but in the waves a flexy tip fin makes for a more forgiving bottom turn as it allows better absorption of bumps in the bottom turn. Thus a lighter rider would prefer a flexy tip, or normal to heavy people in overpowered conditions with a bumpy wave face.
As a heavy guy I use stiff fins for most sailing but at Gnaraloo for example where it is plenty windy and bottom turn control is more important I use a pretty flexy fin
Bit like sail twist I think, the twisting off allows it to dump off some flow and therefore loading on the fin
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