how fortunate!: a teacher's or poet's glad exclamation that a certain kind of person has a life worth envying
This is not really a description so much as a cry of admiration. A wisdom teacher or psalm-singer looks at a particular kind of person, the one who trusts God, walks his way, or finds wisdom, and bursts out, "How fortunate that person is!" The word always opens the sentence and points at a human being, never at God, and it never asks for anything. It simply notices, with a touch of envy, that a life lived a certain way has gone well.
Underneath the exclamation sits an old picture of walking the right road. The word is tied to a family of terms about steps and going straight ahead, and the wisdom writers play on that: to be on the right path is itself the good fortune the word celebrates. Psalm 1 spells this out, holding up the way of the upright against the way of the wicked, and the opening cry "how fortunate" simply names what that good road leads to.
The one sense covers a wide field of human flourishing, from the person who fears God and delights in his instruction (Psalm 112:1; Psalm 119:1), to the one who is corrected and learns from it (Job 5:17), to the nation God has saved (Deuteronomy 33:29), to the servants who get to stand near a wise king (1 Kings 10:8). The shade shifts with the context, but the move is always the same: a glad, observing congratulation on a life that is going the right way.