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No time to work on it for the near future, sorry.
You're as likely to work on these as I am not, I guess. I have no time for core/javahelp development. Maybe you will at some point.
Tim, you could take this if you want, though it touches more on the invisible infrastructure of the help system, which I will probably maintain...
Should be handled by JavaHelp 2.0 automatically; see issue #36253.
Fixed as part of issue #36253.