Then they can update their playback engine to support gapless playback while they are at it.

Good to see that so many other people on this forum feel the pain caused by the lack of this feature in iTunes. About 30% of my music collection are continuous mix recordings.
Seriously -- my senior project in college was writing an audio playback application for live performace. It was far from elegant, but it supported the equivalent of gapless playback.
Of course the playback engine was designed for playing multiple audio sources simultaneously and "mixing" them together into an audio output stream, but in my eyes the solution for iTunes is just a simplified version where there are only two audio sources. The problem of AAC / MP3 frames that someone mentioned earlier could be solved by writing a byte marker for the final frame of each track to the file during importing. It would indicate the end of the track and allow for gapless playback. Trying to "detect" the end of a track is a bad idea since many recordings include intentional silence which should be preserved to reamin true to the recording.
That my 2 cents on the issue anyhow.