Yeah, now that I was aware of it, I saw it three more times today.

Before I posted last I was driving home listening to Josie and the Pussycats. Before pulling up in my driveway I switched playlists to listen to Linkin Park's Meteora. When I left for school it was back on the last Josie song I was listening to. I switched back to Linkin Park for my drive to school (listened to about 6 tracks).

Next I leave school to come back home, my empeg is playing a random song from the Josie soundtrack, not the one before!.

Right before shutting off my car and pull out my empeg, I'm into Rush 30 seconds, pull and re-insert my empeg, and it restarts with the same Rush song, but at 15 seconds.

I also noticed when selecting a new playlist, while another song is playing, it doesn’t stop playback to switch immediately like it did in 2.0

So I'm convinced it is a bug, although not a show stopper I will continue to use alpha 5. At first I was afraid of the crossfade, because I hated how winamp did it, but am pleased with the time being adjustable. 1/2 second suits me perfectly! Since I haven't no-gaped my MP3's, that addition is really cool too!