Rick, is there a special skin you use for DJing on winamp? Just curious how you have it set up for this use. Are you just creating a playlist and letting it roll?
No, basic skin. I setup 2 PCs, each with winamp. I then replicate the major event songs on both units and play them in sync (start one, then the other) in case of some kind of PC failure. Incidentally, I have had a bad memory chip cause a system crash but never winamp.
On winamp, I have it set to crossfade with a 5 second lead time. I can snag songs and throw them into the list, rearrange, etc. I usually do full song plays but if mixing is needed, just use the 2nd laptop. If I'm running it like usual, during dinner I'll have a Sinatra piece running on loop. During dance, I'll have a hip-hop piece looping continuously. If I were to lose the 1st machine, just hit the fader on the 2nd unit. After losing that memory chip, no way would I trust a single machine ever again, and for you Mac guys yes your Mac can have machine problems as well. You should always be prepared with a hot backup in place, IMHO.
Incidentally, not that anyone cares, I wanted to share my history with winamp. I started using it in my pre-DJ days, when I was doing a live, solo-act thing. I'd cut tracks without the electric/lead guitar and lead vocal. Later, I got to syncing homemade videos to my performance tracks. Winamp had a really nice way of handling the video where the video screen could be broken out to display on the projector. When the video track was done, the video window closed and I kept using audio-only winamp on my main laptop screen. I know there are lots of nice features of dual-deck, software media players but I've never been convinced of the actual benefit over what I'm currently doing. And there you have it why I'm a DJ hack who uses winamp to DJ professional jobs with.