For dialog & ability checks, I feel like failing is part of character design, and if I've chosen to sacrifice charisma for constitution, then I should play the low CHA path. There's always revivify, but I have scummed over real death. Sometimes, I'd look up the game consequences of success/failure, and it's never game-breaking. For all the 'choices have consequences' talk, you still have to be able to finish the game. That said, years of RPG experience has taught me to always have a max CHA talker and a max DEX lockpicker.
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