If you are not already on the Sonos music system, another cool option (and possibly cheaper) is the Olive Musica, or their Symphony.
This little box will convert your CDs to your chosen format, including lossless, store it on the internal hard drive, and play it back for you. It has PC and Mac compatibility and can auto-find music on your home network. If you have old media, like tapes and records, you can record them directly to this hard drive.
It has an optical out to get your music to the amplifier with the best quality, and you can purchase remotes for each room in the house, which enables playing different music in every room of the house.
The 160GB Musica is going for $1099 on the website, the 80GB (the website is not clear on this) version is $899, and the Sonata (the remote that can go in a separate room) is $199.
Of course its marketing speak, but they have a bunch of audiophile types that are quoted as saying this is a great machine.
For my pennies, though I am looking at this as quite a value over the aforementioned Sonos, especially if you already have stereo amplifiers in the rooms where you want them (part of the cost of the Sonos system is that they have integrated amplifiers in each unit).