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"I wonder he didn't marry her and get all the property," said I. (22.59)
Pip can't understand why Compeyson would walk away from the opportunity of owning land and of being married to a lady, because (we think) he doesn't understand yet that owning land and marrying a lady won't make him a gentleman. Pip still think that money can buy acceptance—but he's wrong.
He had grand ideas of the wealth and importance of Insurers of Ships in the City, and I began to think with awe, of having laid a young Insurer on his back, blackened his enterprising eye, and cut his responsible head open. But, again, there came upon me, for my relief that odd impression that Herbert Pocket would never be very successful or rich. (22.72)
Pip thinks he's an expert on who's going to make it in life just because he's obsessed with status and wealth—but he doesn't really know anything about wealth or money yet, and he won't until he loses it.
"Then the time comes," said Herbert, "when you see your opening. And you go in, and you swoop upon it and you make your capital, and then there you are! When you have once made your capital, you have nothing to do but employ it." (22.90)
Herbert's concept of money and wealth involves usability. He doesn't want to own things just to own them; he wants his money to lead him to new ventures and to expose him to new places and ideas. Not Pip. Pip's concept of wealth and fortune is tied to an image of Miss Havisham's world, but her world is a stagnant one in which time has stopped and nothing grows. It's no coincidence that Herbert's capitalist concept of wealth made England so powerful in the nineteenth century. (And Dickens totally knew it.)