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[Stupid Loserman]

You get a beat for voluntarily accepting a dramatic failure. You don't get a beat just for dramatically failing. If, for example, a penalty reduces your dice pool to a chance die, and you roll a 1 and suffer dramatic failure, you don't get a beat for that.

Same deal here: no beat. The voluntary beat is offering a carrot. In this scenario, you're just getting hit with a stick.

[Stupid Loserman]

I realize this is just a typo and you meant to say "prepared" or something, but I think you got it right the first time. Paradox always intended to focus on multimedia licensing, but they spun White Wolf off into a sister company and gave it to Tobias Sjogren and Martin Ericsson to manage. And from the beginning, Martin was speaking very excitedly about a long-term plan to revive the World of Darkness itself, not just through multimedia licensing, but through in-house books. He may not necessarily have planned every single fifth edition release to be in-house, but he clearly planned...

[Stupid Loserman]

First Edition, I'm assuming, since Second Edition has freeform vices and you could just put down Sadistic.

For First Edition, pay less attention to the name of the Vice and more attention to the particular Willpower trigger described.

Wrath is better for a character whose vice is a hair trigger, who doesn't necessarily intend violence but spontaneously initiates it when provoked.
A sadist who derives satisfaction from causing particular kinds of suffering or punishment to other characters is a good candidate for a nonsexual manifestation of Lust. This is for characters...

[Stupid Loserman]

A roll to affect another character should be resisted if its effect is primarily limited by the number of successes rolled.
It can also be resisted if its effect isn't too oppressive and a subject successfully targeted can still reasonably work around it, or in other words, if it's just generally more interesting if it's likely to succeed and not worth slowing down with an extra roll.

Anything else should be contested. This primarily includes effects which are significantly manipulative or debilitating and are mostly binary in nature: either it happens or it doesn't.