Let’s start with this: the beatitudes are not meant to make you feel like crap.
They are not some holy benchmark to which you are screwed if you fall short or insta-pious if you don’t. Rather they are a sort of guide which leads us to the revelation and transformation of the beautiful Kingdom of God in the world. 8 principles which show us what a life of joy, justice and reconciliation can begin to look like.
Carrying that, the first beatitude is not saying you are only blessed if you’re poor. Nor is it placating the needs of the poor by a feigned blessing. Rather, this beatitude is addressing the notion that when we have nothing, we have everything in God. It is stressing the ways that we depend on things in our life (jobs, money, possessions, our abilities, etc.) and that when we strip those away we are left with no choice but to fully rely on God: a position which will always be to our benefit.
In many ways its similar to what we see of Link in nearly every Legend of Zelda game. Link’s heroism is highlighted by the fact that he comes from nothing: he is an orphan who has little more than the clothes on his back. Yet this poverty of possessions and ability allows him to fully give himself over to the power of the Triforce as it is imbedded in the Master Sword. The result is that Link is infused with a power that is far greater than anything he could have ever achieved on his own. Because of this he is continually able to defeat Ganon and the forces of darkness to usher in peace and prosperity to the land of Hyrule.
We are blessed in our poverty not because of some divine pity for our weaknesses, rather we are blessed when we are poor because through God we have more power than we could ever have on our own. We have the power to usher in this great Kingdom of God, to defeat the forces of darkness in our own land, and foster peace in the lives of people everywhere.