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script

// Add a function to replace substrings in a given range.
String.prototype.splice = function(start,length,replacement) {
	return this.substr(0,start)+replacement+this.substr(start+length);
}

// Grab the full line(s) which span the selection, as an array.
var lineRange = editor.getSelectedLineRange();
var selectedLines = editor.getTextInRange(lineRange[0], lineRange[1]);
var shrinkSelection = (selectedLines.slice(-1) == "\n");
var lines = selectedLines.split("\n");

// Set up some RegExps and useful strings.
var uncheckedRE = new RegExp(/^(-\s*(\[\s\])\s*)/, 'i');
var checkedRE = new RegExp(/^-\s*\[x\]\s*/, 'i');
var uncheckedPrefix = "- [ ] "
var checkedPrefix = "- [x] "

// Check or uncheck each line as appropriate, accumulating the new lines.
var newLines = [];
for (var line of lines) {
	var checkedMatch = checkedRE.exec(line);
	if (checkedMatch) { // This is a checked line.
		// Uncheck this line.
		newLines.push(line.splice(0, checkedMatch[0].length, uncheckedPrefix));
		
	} else { // This is an unchecked line, either with an empty checkbox or none.
		uncheckedMatch = uncheckedRE.exec(line);
		if (uncheckedMatch && line.length > 0) {
			// Check this line.
			newLines.push(line.splice(0, uncheckedMatch[0].length, checkedPrefix));
		} else if (line.length == 0) { // Empty line. Keep as-is.
			newLines.push(line);
		} else {
			// This line has no checkbox-brackets. First, strip any hyphen.
			line = line.replace(/^\s*-\s*/i, '');
			// Add checkbox hyphen and brackets, unchecked.
			newLines.push(line.splice(0, 0, uncheckedPrefix));
		}
	}
}

// Replace the selected line(s) with their transformed versions.
var newLinesChunk = newLines.join("\n");
var selectionLength = newLinesChunk.length;
if (shrinkSelection) {
	selectionLength = selectionLength - 1;
}
editor.setTextInRange(lineRange[0], lineRange[1], newLinesChunk);
editor.setSelectedRange(lineRange[0] + selectionLength, 0);