Faustian Pact Questions

[AvatarVecna]

I am to understand that a Pact Certain just sells your soul directly for...whatever you sell your soul for. Needless to say, multiple Pacts Certain probably leads to a situation like this (https://www.youtube.com/watch?v=jKH52FNFP9s), which I imagine there's some kind of clause in the contract to prevent. But comparatively, a Pact Insidious basically trades stuff you want for evil deeds committed, with no soul-selling involved; the idea is that the fiends get your soul in the end because you do so many evil deeds that it corrupts your soul so much that it's basically guaranteed to go to them. I have a few questions about Pacts Insidious:

1) Are there rules preventing multiple Pacts Insidious on the same character? It seems that as long as I'm maintaining my evil deeds enough to maintain all the contracts, I can reap the benefits, but I'm not sure.

2) Would a fiend be able/willing to make a Pact Insidious with an intelligent undead, as long as they could end up being destroyed, or would they refuse on the grounds that you've taken steps to avoid dying at your normal time (even though you could still die)?

I imagine either of these could very well be DM judgement, but I wanted to know if anybody knew of a RAW answer to these, because I was unable to find anything one way or another.

[Telonius]

1) I don't believe there would be. I imagine there would be some wrangling about who gets the proper credit for the soul after it's harvested. For example, if one of the signatories were allied with Mammon and one with Belial, they'd want to hash out who gets the soul.

2) would depend entirely on how your game treats intelligent undead (and maybe even the particular kind of undead, like vampire vs lich): do they have an individual soul, or don't they? If they don't have a soul, then a Faustian Pact wouldn't usually make any sense. The devil wouldn't be getting anything in return - with the possible exception of having a good idea what a particular intelligent undead is going to do. (Could be useful in some kind of overly-elaborate, Xanatos- or Asmodeus-level scheme, but not usually relevant).

If Undead do have souls in your setting, the devils might want to make a bargain, but it would probably be a little different. Unless you're talking about Deathless (or other weird non-[Evil] undead), their soul is probably already bound for the lower planes. They'd want to ensure that the target acts Lawfully, rather than Evilly, to make sure they get to Baator and not the Abyss.