I've hooked my iPod Nano to the tape input on a couple occasions. The results are not exactly stellar, which I've attributed mainly to the 990 doing its job - in the process revealing the limitations of lossy compression and iPod's headphone output. I've heard others say that using a docking station to connect the iPod gives better results because it bypasses the iPod's headphone output, but I never bought a docking station to test that out. Upsample probably won't do much good, since the damage has already been done before the signal reaches the 990. I used 7 Stereo mode when I did it, since it was serving solely as background music during a party.