PowerBook G4 + Apple Express + iTunes +? to analog

My goal: Optimize my wireless Mac system to rival the quality of my Arcam CD192 CD player (running into an analog Arcam amp).

This isn't (yet) a question about brand recommendations (e.g., external DACs). At this point I simply need some help understanding how the system should be configured and what types of items I have to buy. I've already decided not to go with SlimServer or Sonos because I prefer to use my existing Mac computers + iTunes + Airport system as my source.

Current setup:

Office/server room:
1. Power Mac G5 dual 2.5
2. Lacie 500GB external drive (holds the Apple Lossless files)
3. iTunes running on the G5 ("iTunes Music Sharing" enabled)
4. Airport Express (802.11g) used as base station/Internet router

Listening room:
1. PowerBook G4 (next to listening chair, with iTunes channeling the shared playlist from the G5)
2. Mac out: analog 3.5mm headphone jack + RCA adapter
3. Amp in: analog RCA jacks on Arcam FMJ A32 + Dynaudio Audience 72 speakers

The audio quality with this set up actually is quite good on first blush. A/B comparisons with the Arcam CD192 are difficult, partly because the Mac source is about 5% lower in volume. I suspect that the Mac source is slightly less "authoritative" or "robust" than the CD player, but because I have to increase the volume of the Mac source to match the volume of the CD player, I can't be entirely objective. I also suspect that the Mac source might be somewhat fatiguing, but this could be due to the higher than normal volumes I used for A/B testing. So, while I'm not entirely convinced I actually need more components, I'll accept the conventional wisdom that an external DAC would overcome any deficiencies, fatiguing or jitter in the Mac source.

My questions:

If I buy an external DAC,

1. Must I buy an additional Apple Express for the listening room, or can I simply hook up the DAC to the PowerBook? (I would need a 24 foot cable to get from the PowerBook to the DAC/Arcam amp. An Airport Express could be located about 3 feet from the DAC/Arcam.)

2. Which type of DAC input -- USB, Firewire, or optical -- is recommended for this setup? Does the answer depend on distance from the digital source (question #1) or on the particular qualities of each connection? Or both?

3. Would I hear an improvement with only the DAC (versus analog headphone jack), or is an anti-jitter box recommended as well?

4. Must I change the way I use iTunes? For example, do I have to make the PowerBook G4 the "iTunes master," so that it directly accesses the library on the Lacie HD over the wireless network? Or is my current "shared playlist" method (using my G5 as the master) OK?

I realize that questions #2 and #3 are probably the most contentious and have already been asked on this forum, so I apologize for the repetition, but haven't seen a concise discussion of the issue of distance. Perhaps I missed it. Feel free to point me to other discussions as needed. Thank you!