As long as calibre is set to update metadata when sending books, the changes should be reflected in the exported ebook when you use Send-to-device.
Unless the book is a dual-MOBI (has both mobi7 and KF8 components).
calibre cannot update the metadata headers in a dual-MOBI ebook.
You would need to use KindleUnpack to split the book into its component MOBI and AZW3 formats.
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