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My main character regularly rolls 30+ (highest I've had so far was 36) on persuasion and intimidation.
My Astarion can't roll below 16 with slight of hand checks unless he hits a nat 1 and also regularly gets 30+.
It's all about stacking proficiencies, skill bonuses, and sometimes spells like guidance, bless, thaumaturgy, etc.
I roll more critical miss 1's than 20s.
Well, in a certain critical plot event I was asked to roll a DC 30 persuasion. It is of course possible to do without but I don't like the outcome - at all. So.. yeah. But okay, your math shows that there are ways around it. I've just missed it. Looks like I can go to something like 12 or 13.
P.S. For the love of donkeys, it's NOT sleight of hand :) That one allows retries given the right tools - almost always (PP isn't my thing anyways)
It's not absolutely necessary though. As long as you don't mind being loud you can use the knock spell to unlock most things, and Dex characters usually have a decent chance even without expertise.
Well not always… netherbrain
My luck would be to keep rolling an 11 lol
Expertise, bardic inspiration, guidance. Advantage helps a ton.