PC-Based Set Up/Process - Comments?

I am finally going to bet around to setting up a PC-based music server for my mid-end system (Rotel components, Paradigm reference speakers, Music Hall CD player, etc.). I am NOT seeking perfect sound. I am seeking a music server system that will sound as good as my Music Hall CD player.

Can you please provide comments with respect to any potential flaws in my system and or process to achieve the above?

- Rip CDs to Dell laptop (La Cie external hard drive) using iTunes in Lossless format (Windows XP environment)
- Play CDs using iTunes
- Airport express connected to external DAC (eg. Bel Canto)

I know that in the past I have heard issues with playback on the PC under windows XP. What specifically do I need to be aware of and how do I solve that?

Thanks to all.

Lawrence