Eight maids-a-milking? You know, I really don't think the objects of the song have any relation to that which they are supposed to symbolize! But these eight maids point to the eight beatitudes: Blessed are the poor in spirit, those who mourn, the meek, those who hunger and thirst for righteousness, the merciful, the pure in heart, the peacemakers, and those who are persecuted for righteousness' sake (Matt. 5:3-10).
These eight "blesseds" become real to me many years ago when I read John Stott's commentary on the Sermon on the Mount, entitled The Message of the Sermon on the Mount (Matthew 5-7: Christian Counter-Culture. Stott lays out the case for a truly counter-cultural community of Christan fellowship marked by radical obedience to Christ. The beatitudes really are characteristics that each Christian, by God's grace, should strive to exemplify. The promises follow as blessings for those who seek after each quality.
I used to trip over the one that says "blessed are the meek." I don't want to be meek if being meek means being a doormat for the world. But I've come to see the strength in humility, in not thinking more highly of myself than I ought, in bearing with the faults of others, and in serving others -- even those these things are a struggle for me.