Actually, I've been playing around with the WinAmp crossfader plug-in, and my experience leads me to prefer almost opposite behaviour.

Songs which have a fade-out and fade-in are often the best to cross-fade; you lose most of the quiet time, the lead-out and lead-in often blend together well and the actual process is usually scarecely noticeable. When you cross-fade between punch-in and punch-out tracks, such as mixed CDs, pretty much all of the time the beats of the two pieces are different and you get a horrible beat clashing sound. Even when the two tracks are in sequence, it's rare that the crossfader actually gets it right and hits the beat spot on; because the actual timing of each beat is independant of the start/end of the song and the length of the crossfade.

I'd still like the crossfading option, but I think it should be applied to playlists - i.e. you can specify whether songs in a playlist are allowed to be crossfaded into/out of.

That's my experience, but it works.

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