I feel that the player's humanity stays way too high throughout the game, despite doing acts that are frankly hineous, if you ponder them for a couple of seconds. Namely I am referring mostly to the quests of the Elizabeth Dane and the Museum most of all, but possibly also "Traffik". In all those instances you don't get penalized by humanity loss, if you follow the frontal assault way; the policemen on the Dane and the guards in the Museum are quite innocent though, they are no part of the Jyhad, they are not out to get you, if they get killed during those quests it is just because they were at the wrong place at the wrong time.
Same pretty much with "Traffik" or the Russian mobsters, you have no previous problems with these people yet you deliberately go there, as part of the quest and can slaughter them with impunity. They are lowlifes perhaps, but they are still human. In fact justifying to one's self that it is alright to kill them because of that, it is already an indication of a humanity rating lower than that of the average person (around 7, your starting humanity in V:TMBL).
In fact coming close to expressing a view of mortals similar to that of Jack, that they are cattle, but that doesn't mean you have to go out of your way to kill them indicates a low enough humanity already (in the P&P I would place that around 4 or 5). Now going out of your way to do it (as you don't really need to in those quests) is way worse.
Minor things that are funny at first sight might also warrant humanity loss; sending that naive thin blood armed with a stake to kill the prince, Nines or the president of the US, taking his money in the meanwhile, doesn't really seem as a moral thing to do, when you know you probably just sent him to his death.
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I find it quite bizzare that I can play a manipulative homicidal maniac and stay at humanity 10 throughout the game, or that I don't lose humanity points for slaughtering two dozen innocent people each time I am too lazy to sneak, while I do lose humanity for nicking small change from a charity box.
Can humanity loss be implemented in quests which you don't finish the sneaky way, like the Elizabeth Dane the Museum etc, or to instances where you do something evil (though probably justified by vampire law) or conniving? What do the rest of you think?