Honestly bro, I think you need both. Have your group of people that does the planned stuff. They meld inconsistent areas. They build onto already established trade routes and waterways, they build new cities atop the old, etc.
Then you have your group that handles the plop-ins, not all people have eyes for details. Some people simply cannot follow another's schemes.
Lastly, and totally optional, you can have a "brush-up" team, that goes along and fixes up the older areas of the game, the ones that need a bit of a boost, or simply the ones that you feel may have changed over time and over constant pillaging by maurading adventurers.
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