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1. Should you soak bark before repotting? Ideally you should soak the bark overnight.This starts the wetting process so the bark holds more water. Also tiny components will settle out to the bottom of the bucket. I have too many plants and do not worry about presoaking. I just water the recently repotted plants more often until I feel the bark is holding an adequate amount of water.
2. Best time to repot is when the orchid is in active growth. Ideally when you see new roots just emerging.