Having rummaged a little, it seems that they can change the size of events not quite as you want.
You can add a resize event like this
$('#content').resize( function(){
or
$('#content').on('resize', function(){
which you already do, but they just don't work when the elements change by javascript code or something like that. the only way to invoke it this way is with
$('#content').trigger('resize');
which you can really do with any string. It spreads through the tree of dominance. Let's say that you had #content inside the body with the "resize" event on both of them. If you call #content, it also calls the body. However, if you trigger an event with a body, it will not fire #content.
However, it looks like you can get the type of functionality you want using the jquery-ui resizable method http://jqueryui.com/resizable/ . After you do something mutable with
$('#content').resizable({options});
it should trigger a resize event if they are resized.
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