The reason why Padre Pio used to tell people to pray to the Virgin each evening in order to enter Paradise more easily, is simply because Mary is the Queen of Angels, who, under her command, have the power to chase away the demons that afflict men, and to repress them, to defeat their enemies. Through the angels, Mary intercedes on behalf of sinners that would turn to her Son.
For Padre Pio, the angels were a very concrete reality. He was always in direct contact with them, thanks to his absolute faith in the Mother of God. And he maintained this connection by praying the Rosary constantly, clasping it in his hand like a powerful weapon. This weapon would help him "to win and obtain everything,” the Virgin promised him.
This is what Padre Pio taught: "Recite the Rosary, and recite it all the time, as much as you can."