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// Additional situations to trigger auto complete
"auto_complete_triggers": [ {"selector": "source.coffee,source.js,source.js.embedded.html", "characters": "$"} ],
would allow $ to trigger completions in coffeescript files, etc. I don't believe the dollar-sign needs escaping in this setting.
But you might need to read the docs to learn when characters require escaping (or double-escaping) in completions and snippets. ST2 is quite clever though as it (for me) dis-colours the back-slashes if I have the wrong number of them. [Edited: Actually, it only does this for me in completions files.]