starting out....wicked budget

What is it about the sound of your system that you don't like? Depending on the Sound Dynamics speakers you have, you may be in good shape for a budget system. What is the "old SS amp"?

Please specify the precise model #s for your speakers (do you like their sound), amp and cd player. You seem most unhappy with the cd player, if so I 'd change that first but no need to go overboard: evolving technology and moving parts mean you'd have to buy another one in a few years anyway. Speakers and amp on the other hand, once you get good ones, are keepers for decades.

Don' feel bad about your budget. Many of us had abudget of 500 for the entire system when we started. Save money and change one component at a time, don't go overboard on anything. Don't waste money on expensive wires, Radio Shack wires are all you need.

Where do you live? Do you have any good audio stores near you?

Assuming you have a newer computer that will run iTunes:
Airport Express with connection kit $170
panasonic sa xr 25 digital receiver $180
Lacie or other external hard drive $150
J and R has all of the above.

I'm running a similar set up with Apple lossless files through a sharp digital receiver. The sound is exceptional (better than my Rega Planet 2k as a transport) plus you can listen to Internet radio.