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Hi ISSATS.
To answer your questions:
No you won’t damage or cause any undue wear on the movement by pulling the crown to handset position several times. The parts in the setting mechanism are designed for this purpose and will handle more use than the watch should actually encounter. Provided you have your watch serviced at the recommended intervals you’re going to be fine.
Your second point is normal, if you pull the crown out at the exact moment the balance is in its centred point it may not have enough potential energy in the hairspring to cause the balance to move on its own when you push the crown back in. A gentle shake from side to side will get it moving again, or like you have found, pull the crown out and in again.
Hope this helps.
All the best
Scott
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