When the album has a nice finale like that medley its nice to let it play all the way through and build to that moment. When I made mixtapes and later CDs for people in middle school and highschool (and fucking minidiscs, remember those pieces of shit?) I would agonize over the track order. You gotta have a good track order. Letting the musician decide the order of the tracks by playing the whole album is fun and I like to indulge it when I have the time.