Unfortunately you can't play songs on the internal and external memories at the same time. You have to switch between the memories. Try putting most of your songs on either one, so hopefully you can listen to most of your songs
Even if it's not possible with the OEM firmware, it should be possible with Rockbox[rockbox.org]. Rockbox is replacement firmware for MP3 players. Installing Rockbox on an MP3 player is like installing Linux on a Windows computer.
I have a Sansa Clip Plus running Rockbox. I keep all my music on a large card, but I don't think what you describe would be a problem.
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