Airtunes sound quality

I have an iTunes library in my iMac with all the music files ripped from my CDs in Apple Lossless. The iMac is connected to an Airport Extreme as my wireless router and I have 2 Airport Express as repeters. In the iMac I have the Squeezeserver running.
In one of my HiFi systems I have one of the Airport Express connected via Ethernet cable to a Squeezebox. The digital coax output of the Squeezebox is going to a Genesis TimeLens De-Jitter and from there to my PS Audio PerfectWave DAC. The output of the DAC is feeding my Woo Audio tube headphones amplifier.
Last night I connected the digital Toslink output of the Airport Express to the Genesis TimeLens to then follow the same sound chain as above.
I compared the sound of the exact same song (file in iTunes) one from the Squeezebox and the other from Airtunes. To my surprise they sounded different. The sound using the Squeezebox chain was significant better. More focus, better bass, more realistic and with better texture. The sound using AirTunes was lean and difussed with a huge and un-realistic soundstage.
I don't undrestand if I am using the same source file and the same electronics from the Airport Extreme on why it is so different. I tried the equalizer route with minimal success.
Is iTunes or AirTunes doing something in the processing? I would liekto eliminate the Squeezebox solution but not at the cost of quality of the sound.
Message was edited by: Musicman159

I am not a big fan of using the AirTunes feature of iTunes because it is not Applescriptable and because you can only output to one stream at a time. The sound quality is quite good as far as I can tell. The only time it suffered is when I was using iTunes on my laptop that was playing from the shared music on my server. The stream would get choppy and sometimes choke, but it is working better after changing my wireless router channel to the other end of the spectrum.
It is really nice that it outputs to optical, preserving the digital signal and eliminating the need for expensive shielded cables to reduce noise from all the other wires behind my stereo.
If I were to do it over, I would have saved the money that I spent on airPort Express to use on my irTrans project.

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