The Cross conquers in the same way as Christ's Cross conquers. It will be brutal. The vision shows him moving through an Apostate Rome. We know this because he stops to bless the "dead". In Churchspeak these are apostates, secularists, pagans, perfidious people. If they were faithful they would be said to have fallen asleep. The Cross is on the top of the hill as Calvary and more than likely represents how difficult it will be to get there. This is I believe what James meant.
My 2 cents. This does not mean we all live happily ever after and the Church returns in splendor to Rome. Fr. M. Martin that knew what the secret said in one tape said, we do not know what is coming now, because the secret wasn't released, and the Consecration was not done. Next will be something completely different. I have no idea what. He also said if the secret was made known all the Catholic Churches in the world would be filled with people, begging for mercy. We know Christ and the Truth He has revealed will not change, but the physical entity of the Church is up for grabs.
In Apocalypse 12, the sign seen in heavens, the woman, is a pointer seen here in the Church to something coming. She would not be a sign if she were some obscure meaning thing, and if in Heaven literally she would never be seen. So it's something we in the Church will see.
James believes the Red Dragon is Red China. I do not. It is the Leader of those in the Church seking it's ruin. China might unleash a World War but that isn't a sign. The Red Dragon is another sign in heaven or the Church, as we can't see what is going on in Heaven. He drags down a third of the Stars. That's the Bishops into Schism, if the Consecration is not done.
The man child is a reformer Pope, that was to rule all nations with an iron rod, and he dies, and he is caught upto heaven. The Church flees into the desert or wilderness. It does not talk of another Pope but speaks of Michael and the Red Dragon at war. This is as much as I can decipher at this moment in time. All of this is just my mind at work and should be taken with a pound of Morton's salt.