Some land would be worth more than other of course, resources, rivers, passes, etc. I just hate Culture or Prestige. What the hell is that really? What is the real world equivalent to those? It doesn't seem realistic. I think the US produces a lot of "Culture", celebrities, movies, TV shows, but does that change our national borders? Does prestige? I don't think so. Wars do. Appeasement does. Negotiation does. Nations buy and sell land, they fight over land, they negotiate land. Those things change borders, not culture or prestige.
Yes, but generally it's the people who live on the land that actually do stuff rather than the land itself. Cultural boundaries represent the influence of a government, which generally extends beyond it's national border. Doesn't matter where you arbitrarily draw the line on the map, if the guys on "your" side of the line are more likely to listen to the government on the other than your own. It's probably not as apparent in the Americas due to it's history, but if you look at the border regions of Europe for example you can see it in effect (particularly when you get down to regional levels).
It's problematic because games tend to roll up the concept of influence, culture and borders into one, but any way you implement it you can argue is just as silly. Generally speaking borders tend not to be quite so solid as they look on a map, particularly for the population in the area. It really depends on what the gameplay effect of the border is; given the subject matter the approach of Age of Wonders might make the most sense - your border stops at the point your sovereign's spell casting range does. After all, a mountain range or river isn't much of a boundary if you can instantly teleport troops over it.