What really grinds my gears is that metadata on pictures you have in iCloud gets stripped when downloading to Windows. I take pictures of stuff for work and label them to know what the hell I'm looking at, but the descriptions disappear on file transfer.
So I gotta either:
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Re-add in the description in the metadata
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Label something else, like a sheet of paper or something and put it in the frame
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Manually name each individual file after transfer, which is just as laborious as adding back in the metadata.