I've recently learned that milestones are meant to span the entire 6-month 🌬️ drop period. I think it's a bad idea, at least with their current structure
Milestones are easy to achieve, so if they don't reset, we are extremely incentivized to create multiple alt accounts to continue participating in the 🌬️ drop
Anyone who plays a lot during season 1 won't have anything to do in the subsequent seasons if the milestones don't reset
I know the whole system will be reworked for season 2, and perhaps there's a way to make milestones challenging enough to last 6 months. Still, I think the simplest solution is to reset them every season