I don’t care one way or the other, as long as all of the “fade” contains actual sound. I hate songs that go on at the end with silence for several seconds. More than 2 seconds, I clip the MP3 to shorten it. Ditto for beginning with silence.
iTunes does that automatically, and I just loathe it. It can really screw up the feeling of a song when they make it end abruptly and slam into the beginning of the next track.
iTunes never has for me, I get the full songs played down to the last data bit…there is probably a setting to control that (though I can’t hunt for it now).
I believe that’s the “Crossfade playback” in the Playback tab in the preferences.