Tag ids must be unique. You are updating the span with ID 'ItemCostSpan' of which there are two. Give the span a class and get it using find.
$("legend").each(function() {
var SoftwareItem = $(this).text();
itemCost = GetItemCost(SoftwareItem);
$("input:checked").each(function() {
var Component = $(this).next("label").text();
itemCost += GetItemCost(Component);
});
$(this).find(".ItemCostSpan").text("Item Cost = $ " + itemCost);
});