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You can import at any time. We generally recommend it most when you're not concerned with AI moves as much, since there will be a flurry of activity as the new algorithms take over. Generally speaking, I would recommend:
-Immediately after the playoffs end/First day of the off-season (AI in fluxx anyways, so have full winter to adjust)
-First day of FA (again, most time to adjust, with likely very few outstanding contract offers)
-First day of the season (rosters already in fluxx, although perhaps importing a day or two earlier might prevent them from wanting to take back someone who was already cut).
There are always some things that will only start populating after you update - for example, you won't be able to see spray charts for any OOTP-19 or earlier games, they will only show "new" data. And as mentioned, the first day you upgrade, the AI will likely have many roster moves. If that's not a concern to you, though, then any day you upgrade will be fine. Worst case they might have a trade or contract negotiation where someone is suddenly insulted by the offer while they may have accepted it before.
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