Trying to structure my intuitions here.
My base model is that there's at least a 40% chance of the Gambler affecting an action like Foundation. If there's a single 1d100 rolled, a 20% chance of converting a failure into a success and a 20% of converting a success into a critical. If there two or more rolls there's an at least 64% chance of it having some effect. And given that I don't think increasing the number of participants would have made the foundations less likely to be successful, I don't think that the argument that because there may be a roll per participant this makes the Gambker less effective is true. If anything, depending on whether the Gambler is applied before or after rolling, having more rolls may make it more likely to succeed as it's less likely to be wasted on an already successful roll.
With the Father option, the following all need to be true to impact on the Foundations.
- Halathea is one of Ranald's daughters.
- The Hedgewise ever knew something relevant about the Waystones
- The Hedgewise preserved that knowledge
- This particularly faction of the Hedgewise preserved that knowledge
- The particular member of the Hedgewise we speak to knows it or knows someone else they know knows it
- Another tradition represented on the Prioject doesn't also know it
- That the Father face of the Coin means that they'll hand over their knowledge without an upfront favour.
- Edit: the unique knowledge they can share is significant enough to make an impact on the foundations
That's an awful lot of 'ifs' that all have to be true for it to come off. It's not like the Gambler where we're talking about probabilistic risks. This is like Knightian Uncertainty, that things are either true or false but we don't know which and we can't make plausible estimates either. What we can say is that an awful lot of things have to have happens in the past in exactly the right way for this to payoff.
The Gambler, by contrast is making that the we get the best result we can from the defined set of pieces that are in play. It depends on what happens next, rather than what happened in the past and we may learn about now.