Cal. 565 Date Quickset (not working?)

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I've watched videos and it looks like it should be fairly simple. Is there a trick to engaging the quick date set? Is this a common failing point? The date clicks over at midnight just fine.
 
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You just pull the crown with medium force and it should engage, there could be an issue or maybe you got a 562 in there instead of a true 565
 
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And don't use it around midnight (+/- 3 hours). That will damage the date mechanism.
 
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Is this any extra wear on the watch with 565 pull quick set from a watch that has a more modern traditional quick set, position and turn?

it feels like it would be more stress popping it out. I don’t do it frequently but it just feels awkward and is possibly stressing the movement
 
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I've watched videos and it looks like it should be fairly simple. Is there a trick to engaging the quick date set? Is this a common failing point? The date clicks over at midnight just fine.

Probably the Date Corrector Yoke is broken.
 
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Is this any extra wear on the watch with 565 pull quick set from a watch that has a more modern traditional quick set, position and turn?

it feels like it would be more stress popping it out. I don’t do it frequently but it just feels awkward and is possibly stressing the movement

No, not really...