The solution I wrote is probably not the best, but it’s working, might be worth to share:

// When dragging starts
start: function() {
// Hide the original and initialize the placeholder ontop of the starting position
$this.hide().after($placeholder);

// Find the deepest nested child
var maxChildDepth = 0;
$this.find(settings.nestable).each(function() {
var childDepth = 0;

var parent = $(this);
while (parent.attr(“id”) != $this.attr(“id”) && parent.attr(‘id’) != $root.attr(“id”)){
if (parent.context.nodeName.toLowerCase() == settings.nestable.toLowerCase()){
childDepth++;
}
parent = parent.parent();
}

childDepth = childDepth/2+1;

if (childDepth > maxChildDepth) {
maxChildDepth = childDepth;
}
});
$this.data(“maxChildDepth”, maxChildDepth);

// Run a custom start function specitifed in the settings
settings.start.apply(this);
},

I had to change all instances of ui.position to ui.offset to get it to correctly detect where the dragged element currently was (eg $item.offset().top < ui.position.top became $item.offset().top < ui.offset.top).

Just thought I’d share that in case anyone else had the same issue.

Lucas, Would it be possible to have every LI either have a class of “haschildren” added or removed based on if this LI has any children?

Per your suggestion above, CSS wasn’t able to work:
ul#task-container li input[type=checkbox] {display: none;}
#task-container li ul li input[type=checkbox] {display: inline;}

The reason being is that CSS hides the check box for root items that don’t have children. I’m not sure how CSS could solve for this scenario without a class set on root. I’d love to hear your thoughts.

Thanks, B