Why should I jump in? Why should I wait? What’s the deal with the seasons anyway?
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I think you should complete the campaign, you most likely still have two weeks before the season even starts. I am not sure about this, but i believe to unlock freeplay for your seasonal cahracters you have to finnish the campaign
Seasons are a way to let all players start at the same point at the same point. They only thing carrying over from your non seasonal characters are the shrines of lillith that you found as well as your capaing finnish.