I am listening to my Squeezebox now and have been all day. My Transport is sitting there powered up but I am sitting on the couch with my laptop in my lap jamming away..
Itunes has impacted my listening quite a bit, since I work more than I am home. I have a pretty nice setup at work, Quad Intel MacPro/30" Monitor connected to project headamp/sennheiser 600's and a panasonic xr50/b&w 602. I can listen all day at work to my lossless files, and the sound is really good. When I get home, I listen to my main system but end up missing the ease of selecting music vs. digging through my 8 224 cd binders finding the disc I want. The random function allows me to revisit cd's I have not listened to in a long time. My next step is to add a iTV to my main system.
A couple of points of clarification for anyone who hasn't explored the option of putting your music on a hard drive.
iTunes and mp3's don't necessarily have anything to do with each other. iTunes is an application that runs on either a PC or a Mac and is used to organize and play music files. Those files can be in any of several formats, including AIFF, the same files that are on your CD's. You can also manage mp3's or several other file formats but the choice of quality and file size is entirely up to you.
In the same way, the iPod and mp3's don't necessarily have anything to do with each other. It's possible to store and listen to many different file formats on the iPod, from uncompressed files identical to the originals on your CD's to highly compressed mp3's. Again, it's your choice, based on what kind of fidelity you require and how much music you want to store in a given space.
And, it isn't necessary to have an iPod to use iTunes. iTunes is the tool you to load music to an iPod but it works wonderfully well on it's own to play music through any of the devices recommended in the posts above.