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The Stormrider brothers can't afford to remain stagnant for long. They can rest, but they can't stop.
Their first Hell Dive experience sure was traumatic. Experiencing a horrible death from the maws of the endless undead horde was harrowing, so nobody could blame them for being scared. However, their petulant pride and the fact that Hell Dives will be a constant part of their lives now prevented them from retreating. And so, despite their fear, they have to keep moving forward. Especially since this will happen again next month.
Gerald was at a loss...
It's not that he's running out of ideas; it's simply because none of them were going right as he intended them to.