The High Places of the Earth

Then shalt thou delight thyself in the Lord; and I will cause thee to ride upon the high places of the earth, and feed thee with the heritage of Jacob thy father: for the mouth of the Lord hath spoken it. (Isaiah 58:14)

He shall dwell on high: his place of defence shall be the munitions of rocks: bread shall be given him; his waters shall be sure. (Isaiah 33:16)

He made him ride on the high places of the earth, that he might eat the increase of the fields; and he made him to suck honey out of the rock, and oil out of the flinty rock; (Deuteronomy 32:13)

When Isaiah 58 speaks of the high places of the earth, I suppose the most logical explanation would parallel Isaiah 33 where a high place is described in reference to how safe and secure it is from enemies. This could well be the fundamental significance of the high places of the earth.
But in Deuteronomy 32 we see a long passage, describing Jacob which Isaiah 58 refers to, where the exact same phrase is used: ride on/upon the high places of the earth. The context describes Jacob's great earthly success given to him by God. Yes, Jacob worked hard for his success, yes, Jacob had his troubles. But God blessed him. I'm not about to preach some prosperity gospel. But to say the phrase  ride upon the high places of the earth, and feed thee with the heritage of Jacob thy father has nothing to do with visible earthly success would be unkind to the clear word of God.
When we fulfil the conditions set earlier in Isaiah 58, we will experience the success we really want: that is the gospel going to the whole world and Jesus' return in our lifetime.