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On the upside, with just a few light taps of the bullet puller I can get the bullet to come out just a bit but still stay in the brass, so I can just seat to the proper OAL without having to harvest the de-loaded powder and recharge everything.
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I'm wondering if you could see a mark on the bullet plating from the first crimp. I suspect the plating deformed if the first crimp was heavy. Just check to make sure the plating wasn't "cut through" to the lead. I don't think the plating would peal away with the lower velocity .38, but strange things do happen....