questions on pestilence-type damage

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couple of questions on how damage from Pestilence works:

1. I have a Mistmeadow Skulk. If my opponent pays a black mana for Pestilence, is the Skulk protected? Because the damage is coming from an enchantment whose converted mana cost is 4. But it does not target the skulk though.

2. My opponent has a regenerator, like Drudge Skeletons. Can he say something like "I tap 5 mana. With 4 of it I Pestilence, and with 1 I regenerate the skeleton."? Or does he actually need to Regenerate for each individual 1 damage of Pestilence?
1. I have a Mistmeadow Skulk. If my opponent pays a black mana for Pestilence, is the Skulk protected? Because the damage is coming from an enchantment whose converted mana cost is 4. But it does not target the skulk though.

One of the properties of Protection from XXXX is that all damage from XXXX sources. This means that any damage that a source with converted mana cost 3 or greater would deal to the skulk gets prevented, including damage from Pestilence.
2. My opponent has a regenerator, like Drudge Skeletons. Can he say something like "I tap 5 mana. With 4 of it I Pestilence, and with 1 I regenerate the skeleton."? Or does he actually need to Regenerate for each individual 1 damage of Pestilence?

He would need to regenerate once for each activation of the Pestilence, because each of those activations will result in 1 damage being dealt to it which would cause it to be destroyed. If he only regenerates it one time, then only the first Pestilence ability to resolve will fail to destroy it. Then the next one to resolve will deal 1 damage to it again, and it will be destroyed.
1. Protection protects against [D]amage, [E]nchanting/equipping/fortifying, [b]locking, and [T]argeting. Pestilence is dealing damage, so protection from CMC 3 or greater will prevent the damage.

2. He must regenerate for each activation of Pestilence which deals 1 damage to it, which is lethal damage and will cause it to be destroyed. One regeneration shield will only prevent it from being destroyed by one activation.
Also, to clarify, you don't pay X black mana for Pestilence to deal X damage to each creature and each player, but you activate Pestilence X times, each time paying , which will result in it dealing 1 damage that many times.
1. I have a Mistmeadow Skulk. If my opponent pays a black mana for Pestilence, is the Skulk protected? Because the damage is coming from an enchantment whose converted mana cost is 4. But it does not target the skulk though.

Protection does several things. As you seem to know, one of them is prevent targetting, and you are correct that pestilence does not target. Additionally though, protection prevents all damage from sources with, in this case, "converted mana cost 3 or greater", so the damage will be prevented.
2. My opponent has a regenerator, like Drudge Skeletons. Can he say something like "I tap 5 mana. With 4 of it I Pestilence, and with 1 I regenerate the skeleton."? Or does he actually need to Regenerate for each individual 1 damage of Pestilence?

If it is a 1/1 creature, he will need to regenerate it for each time it is dealt damage. 1 regeneration shield will save it from being destroyed once, and additional shields are needed for subsequent deaths.
couple of questions on how damage from Pestilence works:

1. I have a Mistmeadow Skulk. If my opponent pays a black mana for Pestilence, is the Skulk protected? Because the damage is coming from an enchantment whose converted mana cost is 4. But it does not target the skulk though.

Yes, the damage will be prevented. One of the aspects of protection is that damage from sources with the stated quality is prevented (targeting doesn't matter in this case, because protection prevents damage in addition to preventing targeting). Pestilence can't kill Mistmeadow Skulk any more than Pyroclasm can kill Silver Knight.
2. My opponent has a regenerator, like Drudge Skeletons. Can he say something like "I tap 5 mana. With 4 of it I Pestilence, and with 1 I regenerate the skeleton."? Or does he actually need to Regenerate for each individual 1 damage of Pestilence?

No, he can't do that - he'll have to regenerate four times. Pestilence's ability allows him to pay to deal 1 damage to everything. This will kill the Drudge Skeletons unless it's regenerated, every time it happens. Pestilence does not allow him to pay to deal 4 damage to everything. He can pay four times to deal 1 damage four times, but that will force the Skeletons to regenerate four times or die.
thanks all. in each case, that's what I thought. you guys are FAST!