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@the-inkspiller I mean, no one is forcing you to use RNG to begin with. You could use a trait system where you either have a “thing you can do/thing you are” or you don’t, and that determines in a binary sense whether you can do a thing.

Like, maybe in an OSR game, the Rogue is literally the only guy who can pick locks. Rogues (and their subplasses/prestiges) get to pick locks, but not the Fighter or the Wizard, regardless of how much DEX they have or how high they roll.

But addressing your point, in a game like D&D 5e where anyone can use any skill at more or less the same proficiency once you get to mid-level (excepting Bards and Rogues with their double down proficiency stuff), I think there should be clear guidelines as to what happens when you fail, and I don’t think you should be allowed to just spam rolls until something happens.

Edge of the Empire (and the other Star Wars games) by Fantasy Flight Games uses a dice pool that introduces additional situational information when a roll is made: https://www.fantasyflightgames.com/en/news/2012/11/19/at-the-core/

I like stuff like that (when we’re talking about games using skill checks at all), systems that shake things up and prevent gameplay from getting stale.

As for rewarding good planning against the fickle dice, assuming you’re designing a system with heavy GM involvement, couldn’t you just advise the GM to introduce advantages or otherwise benevolent fiat if they feel like rewarding the players?