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What happens win condition wise if the last shadow and hunter where to die at the same time? This could happen if a dynamite was to go off and kill them both or a neutral had the machine gun and did enough damage to kill them both with one attack. Would this mean that both hunters and shadows lose or would it mean they both win?

Since Shadow have the win condition of all Hunters dead and Hunters have the win condition of all Shadows dead--they don't specify that at least one Shadow/Hunter has to be alive.

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By a strict reading of the rules, the only requirement is that all of the opposing faction are dead, regardless of whether you or anyone else in your faction survived. Therefore, unless there is an official clarification to contradict it, all Hunters and Shadows win in this scenario.

Not much of a source, but this BGG thread agrees.

This would also mean that if a Hunter kills the last Shadow but also a third neutral at the same time, the Shadows would still win at the same time as the Hunters.

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