Sorting possibly unstable and general jsfiddle/jquery problem
You are using the built-in sort of Array, which is not guaranteed to be stable per the documentation. You will have to write your own sort algorithm from scratch.

Other than that, 


It is considered better form to have a single comma separated var statement
Calling append() inside a loop gives poor performance, just collect everything in a string, and call append() once
You could cache $('#healthplans tbody') since you call it more than once
You should not skip the newline after an if statement
You should consider using hasOwnProperty when using for (item in dataSet[i])
You did not declare item with var
You call too many things item, I am assuming that the property in dataSet is more of itemId ?
All that gives this :

var applyData = function (dataSet) {
    var i,
        itemId
        item,
        itemRow, 
        html = '';            
        $table = $('#healthplans tbody'),

    $table.empty();
    for (i = 0; i &lt; dataSet.length; i++) {
        itemRow = '';
        for (itemId in dataSet[i]) {
            item= dataSet[i][itemId];
            if (typeof item=== 'number') 
              item= '$' + item;
            itemRow += '&lt;td&gt;' + item+ '&lt;/td&gt;';
        }
        html += '&lt;tr&gt;' + itemRow + '&lt;/tr&gt;';
    }
    $table.append( html );        
}



I did not comment on the sort function, since that most likely will be throw away.