Well, I just physically moved the file onto the phone and it's working like a charm.
So that rules out rockplayer or any other media player as the culprit.
I still don't know what the hell is going on and at this point it's either a "compression" issue with the actual files or maybe some sort of "network" issue related to my firewall settings. I'm doubtful of the last one in that I tried different file types (mp3/jpg) and they all showed up on my phone just fine.
Or maybe my phone is too busy trying to kill the iPhone it doesn't have time for my stupid requests.
You'd think the iPhone would be dead by now, what with all the ............erm "killers" that have come after it.