Personally, I've found it to be almost 100% random, particularly with connections. I've always assumed that there were enough steps in the process that there was no way the bags would stay in any particular order.

For the OP, perhaps it's not random; maybe you should consider tipping the skycap next time.

Oh, and being elite does matter, at least on some airlines. Works well for me on int'l flights on UA, but not so much on domestic ones.