It doesn't even have to involve money the fact that he has the land gives him power over others. Also what about colonists? It's apparent not all of them are happy about it so I don't think all of them went because they wanted too. That's why I liked DS9 it knows it doesn't really make sense

But yes, DS9 does also explore it. How it is easy to be angels on a core world where they want for nothing and can just be hedonistic and indulge themselves. Whereas frontiers provide challenges and risks. And anger if the UFP decide your colony is forfeit to appease others.

I don't think it works that way either. He has no real power over anyone as we see it. People would go there just to learn the skills and develop themselves. They could walk away at any moment and choose something else. The satisfaction of being part of the wines production is the goal.