Connect Imac to Stereo via Headphone Jack & 2nd Stereo via Airport Express

I have two whole-house stereo systems; one serving the lower level (basement) of my house and another serving the first and second floors. My iMac is on the lower level. The house was prewired with two coax cables (standard cable TV-type cables) from the area behind my stereo on the lower level to the room where my iMac is located. Using adapters from Radio Shack, I was able to directly connect my iMac to my home stereo on the lower level. I can currently play my iTunes on my lower level stereo by plugging the cable into the headphone jack on my iMac.
I am set up with a wireless network using a Linksys WRT54G. I would like to be able to also stream music from iTunes on my iMac to my home stereo on the first floor. I realize I can do this with the use of Airport Express.
My goal is to be able to play the same music from iTunes on my iMac on both stereos simultaneously. My question is; if I have my lower level stereo connected to my iMac via the headphone jack, will I still be able to stream the same music from iTunes to my upper level stereo via Airport Express? I'm concerned that by connecting the lower level stereo to the headphone jack, the music will not be able to be streamed wirelessly to the upper level stereo.
Thank you in advance for your time.
iMac 24 in. Mac OS X (10.4.8) Wireless keyboard & mouse, Linksys WRT-54G connected wirelessly

Hi.
Assuming your iMac is no more than 50 feet from where you intend to locate the express then:
You will need to configure your airport express to join your current wireless network in client mode (otherwise you won't be able to use the internet and the express at the same time).
http://docs.info.apple.com/article.html?artnum=302153
In iTunes there is an option to select multiple speakers. Thus you select this and then check the desired options. Hence you can have music coming out of the speakers/hadphone jack on your iMac AND out of the speakers connected to the airport express.

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