What Jesus meant with saying that the poor are blessed is something analogous to that the eye is blessed with the gift of clear vision when it is not full of specks preventing it being a window for the observation of reality by the consciousness utilizing it.
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It is not to say that you should avoid wealth and the enjoyment of materiality; only that you should not let these things be an impediment to experiencing the glory of reality as it is, unconditionally.
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When you are always preoccupied with making more money, living in a world of abstraction, you ignore the fact that you are already in Heaven, and the Kingdom of Heaven is not yours.