at what stage do you use the tumbler for breaking - pickle tan and then after oiling and as it is starting to dry or after it has dried (after oiling)
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Either time will do.
You get a papery sounding skin if you do it too late.
Best to break when skins are fur dry, leather damp. About 85%. When you can pull the skin and see white vs. that tanned translucent color.
If you need help understanding any of those big words, look them up.