Consider making a software only trial of the SqueezeBox system. By
which, I mean download the latest released version of SqueezeCenter from
http://www.logitechsqueezebox.com/support/download-squeezecenter.html,
on the same machine you use to run iTunes, and point it at your iTunes
library so that it can do a scan and discover you music collection. 
Browse around in the web interface, and check how much of it was
successfully discovered and categorized.

Then you could try streaming to a software player on another machine
(pref. a WiFi enabled laptop), using SqueezePlay or SoftSqueeze.  You
can get SqueezePlay (beta) from here
http://downloads.slimdevices.com/nightly/?ver=7.3 

You may have a few issues to resolve before everything is working to
your satisfaction and comfort, but once you are in that state you can be
highly confident that your first hardware player is going to be set up
and running in a matter of minutes. Of course this kind of testing only
gives you an impression of the software ecosystem, and does not
represent the experience of having an actual hardware player (which also
comes with support from Logitech staff). 

Pippin is being somewhat modest: I will say that his iPhone / Touch app
is an excellent way to get control of your entire Squeezebox
client/server system from the palm of your hand, and is available on the
App store for a modest fee.


-- 
dsdreamer

----------------------
"Dreamer, easy in the chair that really fits you..."
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