I've added two songs to my playlist so far, The Synapse (Hong Kong Streets) and Return to NYC. I'm having a minor problem, in that their metadata is reporting them to be twice as long as they actually are. The two tracks are both playing properly aside from that.

Are they VBR?

Yes, it looks like it, but I've had VBR mp3s before and it's never done that.

Don't wanna steel kodeen idea here, but..
Might be the VBR headers then? I had a lot errors when i was using wrong tools to rip my music, ending up with a lot of reported 32 minute long songs.
Try fixing them. I use Foobar2000 as my player of choice, and it has a embedded utility for that. Select all, right click, choose Utilities, FIX MP3 VBR header.