Dubious Fortune (3.5e Trait)
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A farmer used an old horse to till his fields. One day, the horse escaped into the hills, and when the farmer's neighbors sympathized with his bad luck, the farmer replied, "Good luck, bad luck, who knows?"
A week later, the horse returned with a herd of horses from the hills in tow, and this time the neighbors congratulated the farmer on his good luck, to which the farmer replied, "Good luck, bad luck, who knows?"
Then, when the farmer's son attempted to tame one of the wild horses, he fell off its back and broke his leg. Everyone thought it was bad luck. Not the farmer, whose reply was "Good luck, bad luck, who knows?"
Some weeks later, the army marched into the village and conscripted every able-bodied youth they found there. When they saw the farmer's son with his broken leg, they let him off. Now was that good luck or bad luck?
Everything that seems on the surface to be an evil may be a good in disguise. And everything that seems good on the surface may really be an evil. So we are wise when we leave it to the Heavens to decide what is good and what is bad fortune, and thank them that all things turn out for good with those who live their lives unbowed by such concerns.
When you roll well, you beget misfortune. When you roll poorly, you beget fortune.
Benefit: Whenever you roll a natural 1, at the start of your next turn you become subject to a blessing of fortune (the inverse of curse of misfortune): you roll every d20 or d% roll twice, taking all the better results for one round, extending the duration by another round whenever a natural 20 is rolled. If a natural 1 is rolled when under the effect of the blessing of fortune, it is not ignored in favor of a higher roll but instead ends the effect immediately.
Drawback: Whenever you roll a natural 20, at the start of your next turn you become subject to a curse of misfortune: you roll every d20 or d% roll twice, taking all the worse results for one round, extending the duration by another round whenever a natural 1 is rolled. If a natural 20 is rolled when under the effect of the curse of misfortune, it is not ignored in favor of a lower roll but instead ends the effect immediately.
Special: During a blessing of fortune, all luck bonuses a character enjoys are doubled. During a curse of misfortune, all luck bonuses become luck penalties instead.
Roleplaying Ideas: You're the luckiest, unluckiest luckiest guy ever, with the worst luck ever. Perhaps you tend to have good luck at the worst times, or bad luck at the best of times. Either way, when it comes to you, karma just can't make up its mind.