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Hello Neil

I'd tackle this diagram in OmniGraffle Pro using a combination of some core shapes (e.g. a circle and maybe an arc or two) and then use some of the boolean shape tools (menu --> Edit --> Shapes) to cut out and / or fuse together the pieces into the right shapes you're looking for.

As to the bonus question - I'm not going to get the points for that one. At the moment OG cannot do that... although many of us hold out hope for an upgrade that will