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If we're talking about a way to generate an upgrade image for a single architecture, taking a known version # of an executable to another known version #, built on a production build machine, I would think that could cover the case easily.

That kind of led to my second question: this makes really small images, but only from one known version to another, right? What happens if the target to be upgraded is 80 revisions behind?

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I can't speak to what chrome does, but usually there would be rollup patches to take advantage of, cutting down the number of patches to apply dramatically. E.g. To get from 23 to 76 you might only need to apply 23->25->75->76. This would be slightly less efficient than going directly both in terms of time patching and patch size, but not terribly so (one can assume most patches are decently disjoint). Most importantly, this keeps the total number of supported patches manageable.

Presumably it's still a known version. Just an older one.

You only need to keep one diff for each version you've previously published. Shouldn't be hard.

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