I've been having the same probs with winamp skipping too. Here's my system:
P3700->973, Asus CUSL2, 256MB PC133 CL2, SB Live Value, GF2 GTS 32MB, Quantum KA 18GB 7.2K, Quantum lct15 15GB 5.4K, Adaptec 2940
Running W2K w/ DX8a, had the same prob when I was running DX7. Messed with Winamp buffer settings, defragged drives, cache the entire song and nada. Can't get the skipping to go away. Starting to think it's SB related, read on the Winamp webpage that it's caused by video card and sound card fighting for bus. Possible because W2K assigns IRQ9 to everything.
BTW is DMA auto for W2K? I remember I needed to do a registry hack to enable it in NT4, wonder if it's the same. Can't find the checkbox like in W98. Any help greatly appreciated. Thinking about picking up the Phillips Acoustic Edge this weekend just to see if it makes a difference, any comments?