If the sleeve needs to be insulated, these washers should be used.That one looks like the sleeve terminal (9) will be connected to the panel it is mounted on. If you're trying to keep 'signal ground' separate from 'protective earth' (a popular talking point, I understand) you won't want this type of socket.
Yes, with that type of socket, there is almost no limit to the switching possibilities, no risk of damaging the source or corrupting ground, except what post #22 exposes.
Nasty because it briefly connects the battery -ve to the tip of the incoming plug, and battery +ve (via the circuitry) to the sleeve. I'm sure a million guitars survive this treatment every day, so it's probably fine in practice.
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