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Coincidentally, I have been catching up on the latest series of Tabletop Deathmatch (well worth checking out) and heard a really interesting point from one of the judges, Luke Crane:
I guess this isn't really rocket science, but I feel I need to make sure I remember it. The context for this was a game where there were situations like, for example, a player's entire turn was rolling a die to see if they passed a challenge, getting a bad roll, and that was it, they had to wait for their next turn to try again. And this happened at least twice in a row. This does not make for riveting gameplay.
It is also worth noting that another judge was commenting about the same game that being successful wasn't very exciting either. I haven't got to the end of the series yet, but I'm guessing that this probably wasn't the winning game.
This got me thinking that a good policy would probably be that in most cases where there is uncertainly of success or failure, either outcome should just open up a new opportunity to develop the game's narrative. Or at least, if you fail, you gain something that may help you mitigate against bad luck later.
Actually, that is sounding quite fun, having a game where failure early on could give you real advantages later. I'm sure that's something to work with.