I tend to read it as a combination of those ideas. Being “poor in spirit” seems less about self-esteem and more about recognizing our need for God. It’s the opposite of spiritual self-sufficiency.
Humility plays a role because it acknowledges that we don’t have everything under control. Dependence is there because we recognize that life with God isn’t built on our own strength. And sometimes brokenness is part of the picture because life itself reveals those limits.
So rather than seeing it as weakness, I see it as honesty: the posture of someone who approaches God aware that grace, not personal achievement, is the foundation of the relationship.
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One of the obstacles to faith in Christ is not believing in Him. And one of the reasons people don’t believe is because they don’t think they need a Savior. They don’t see their sin for what it is. So to be poor in spirit is recognizing what you actually are. It’s an inside look at yourself, your depravity and your inability to love and do what’s right.
With that realization, comes mourning. Some may just walk away from it or muster up their pride to dismiss it, but the one who’s on the path to Christ will mourn when they realize what they are. The mourning brings about an open and gentle spirit of meekness. The pretense is gone. Pride is gone and what they truly hunger for is a righteousness they have no way of obtaining. It’s these people who will be filled.
One thing related to this passage (The Beatitudes) that I recently realized is that Jesus is not so much saying that those who are poor in spirit are blessed, as if being poor in spirit (humble, dependent, etc.) is something to strive after or attain, but rather that a blessing will follow when you find yourself “at the end of your rope,” as the Message translation puts it. It’s a rather small distinction, but it radically shifted my view of this passage because I often fall into the trap of thinking being “poor in spirit,” and all the other things Jesus lists in Matt. 5 are things to grasp after to be more like him. Instead, I think Jesus is all about providing comfort to his followers in this passage. “With less of you there is more of God and his rule,” vs. 3 in The Message goes on to say. It’s as though he’s saying, “Even when life seems terrible and you’re discouraged, there’s a silver lining: God is right there with you.”
Not sure if that really answers your question, but it’s been on my mind and heart lately.