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Maintaining the fork as a stack of patches using something like Stacked Git can make it a little easier than rebasing: https://stacked-git.github.io/

Yes, we would branch from upstream again and apply the patch set against the new branch. Normally it is trivial but once in a while there are manual changes necessary.

I usually have my own branch which can be used to get a diff and maintain the diff on any major code structure change. Most often there is not much hassle but can be annoying.