I'm wondering if there is any way to get items loaded in order? E.G. Sword, Helmet, Chestplate, Leggings, Boots, Sword, Helmet, Chestplate, Leggings, Boots, etc.; or Leather, Chain, Iron, Gold, Diamond? It's rather annoying to go and add in one item at a time.

Try this

Arrays.sort(arrayOfItems, new Comparator<ItemStack>() {
   public int compare(ItemStack item1, ItemStack item2) {
      return item1.getName().compareTo(item2.getName());
   }
});

P.S: this is pretty much just java code. it really isn't that hard.

Thanks for the help! Both of you.