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Ever since Dale rose to a high enough position in Resko, he was given the ability to issue tasks and their appropriate rewards based on nothing but his wishes and the resources within Resko and his own pockets.
At first, he was limited in what he could do, and in a way he still is...
He didn't quite know what to expect of this.
Over time, his Reputation grew, and so did his position.
And the more he explored this 'privilege', the more he came to understand its limits.
Dale understood that with a high enough position, he could theoretically alter how the System worked within the City, as it wasn't just limited to him issuing and creating Quests based on the situation.
With items, powers, and other objects, Dale's level of manipulation increases, as the System will recognize his own capabilities and translate them into 'authority' over it.