In what way do characters regain Willpower through acting according to their nature in VTM/oWOD games?

Question

I am currently running a game that has a Ravnos player in the coterie that uses his Chimerstry discipline and thus spends a lot of Willpower. His Nature is Monster, letting him regain willpower through monstrous acts of violence.

Can Willpower be regained at any time like this? Is it once per session or limited otherwise? And is it awarded immediately or at the end of the session?

I'm just asking because it's proven quite easy to go off and cause utter chaos and destruction and say "Okay, I earned a point of willpower".

Answer 1

Looking to the most recent version of the Vampire: The Masquerade rules (the 20th Anniversary edition), here's what's said about the way that the Monster nature regains Willpower:

Malignant deeds reinforce the Monster’s sense of purpose. Monster characters should pick a specific atrocity, regaining Willpower whenever they indulge that urge. For example, a tempter regains Willpower for luring someone into wickedness, while an apostate earns back Willpower for causing another to doubt her faith. Pick a destiny and fulfill it. Storytellers, be careful with how you reward this Archetype. For example, a player who chooses violence as an atrocity shouldn’t recoup Willpower in every combat, but perhaps only in those that involve wanton destruction, or even cause degeneration checks due to their gruesomeness. Monster is a difficult Archetype for which to offer rewards, and those rewards should come as a result of the character challenging his own descent into the Beast, not rampaging ungovernably because he gains an ever-refreshing pool of bonus dice. (V20, pp.92-3)

It looks like this is a known issue, and there are some ideas for keeping it under check. In particular, the idea that the Monster must put his Humanity (or Path) at risk to regain Willpower from his deeds is one that I've put into practice in other forms, with some success.

As for the general regaining of Willpower, page 267 tells us

Generally, a character’s Willpower pool may be replenished whenever the character fulfills a goal or has an opportunity to restore her self-confidence. Ultimately, specific instances of Willpower restoration are up to the Storyteller. For this reason, Storytellers are advised to be prudent in allowing characters to regain Willpower; it is a powerful and versatile Trait, and permitting players to rely on it too much strips much of the challenge from a story.

It seems the limit on gaining Willpower back is the discretion of the Storyteller. Good luck.

Answer 2

Once you have performed the action you reap the reward. Instantaneously.

For instance, once you drink a subject's blood, your blood pool increases by that amount as you do so. There is no delay. Also, in the case of healing, once so many mintues have passed, you may erase that level of bashing damage you've taken.

Once you've done something monstrous (truly monstrous, not just scaring the neighbohood children with a mask, but actually tormenting them, giving them an emotional trauma that they carry with them) you gain the willpower.

It is very difficult to gain an additional point of willpower by doing the same thing a second time in a row in the exact same fashion. Usually it requires a change of scene or subject. (You cant drain a husk, for instance. It's gotta have some juice left! You can't give care to the guy with the leg you already fixed, it's fixed! Psychoanalyzing him so he doesn't have night terrors is acceptable, however.)

source: personal experience, Werewolf, Mage, Orpheus, which used nature/demeanor.

Disclaimer: White wolf is not known for "Crunchy" rules that have a strict codification. As such, many take liberties with such hazy ideas as regaining a mechanical advantage when roleplaying a particular event or type of event. These have been the rules that I was taught and consistently the ones that were reinforced. Once I get home and actually go back through my copy of Vamp', I will be able to quote the willpower passage for you.