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Compare compression: gzipping individual files vs. gzipping tar of same files

A much more important reason to do what you suggest--despite the loss in compression--is recovery of a corrupt archive. If you compress the entire archive together (ie., tar cf - * | gzip > foo.tar....
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Does it make sense to add checksums to archived data?

It makes sense to checksum those on the file system which you know it's not corrupt in an archive format, and then when written to the other media to checksum it there to ensure it's not changed. The ...

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