Caravan System - No System Survives Contact With the Player

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I personally wouldn't care. If the game overall is better off for it - bring it on.

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Is it even that interesting if you literally have a system telling you that they're doing something shifty? I'm not that big of a guild spy/diplomat, but that doesn't seem all that fun.

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I mostly agree with this too, but I also believe sometimes it is necessary to nudge, using some smaller incentive or disincentive. Otherwise things get out of hand.

Specifically my opinion is 'If players find a way to avoid engaging with one system that is strictly better, let it rock. When the EFFECT of that then starts to push on another system, push back. Only one domino allowed at a time.