My experiences with the above scenarios: you have to remember which player you have the playlist on. If Player A is the one with the playlist, just hit the "sync" button in the dropdown box at the top of the SC webpage window and select "Player B." Then B will start playing A's playlist. As for your second scenario, my setup does not work in the way you are envisioning. In fact, say I've sync'ed Player B with A as described above. If I turn off A because I leave that room, B will continue playing A's playlist anyway, it won't stop playing. And B will resume the playlist where IT left off, not where A left off when I turned off A.
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