Holding and fighting for terrtories, earning money, relationship management, unseen violence, all good premise for a good small scale grand strategy game. Did anyone ever consider this?
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There's a lot of ideas in the office about various new games.
Gangsters: Organized Crime is what you're looking for. It is old, buggy and unbalanced though--but still one of my favorite games and spent many hours just trying to figure out how to play it-. There was no one particular way to play the game, it was one of the first strategy sandboxes that I can remember. Always wanted to see a respectable remake; Gangsters II was over simplified to the point of being dull and Omerta was just garbage.