Li Shenron
Legend
And that die happens to be a d20, to ensure the die roll truly matters: that every hero can fail and every hero can succeed! Sure, the fighter might succeed more often, but it's not like in real life where one person would realistically always win and another person always lose.
But this is not what I want.
Rather, I want challenges where one person would sometimes win and another person always lose. As in "if the Rogue doesn't pick this lock, nobody will". But I still don't want the Rogue's success to be automatic!
The d20 RAW makes this hard to achieve, because in order to make the unskilled person always fail you need to increase the DC in a way that then it makes the probability of success too low also for the skilled person (so it's not anymore just the occasional 'fun' failure for the skilled person, it becomes too often that it isn't fun anymore). If you decrease the DC to re-instate a reasonable success chance for the latter (but definitely not too near an auto-success), you give enough chance of success to the unskilled PCs so that anyway the party as a whole will easily succeed even if the Rogue fails, making it (as you say) pointless to even roll dice.
[I am not considering cases when I am fine with just an auto-success. I am strictly referring to when I do want randomness in the outcome. And no, they don't always need to be larger-than-life tasks for me to want them random. I thrive on adventures where the plot has myriads of micro-twists and turns depending on both player's decisions and a bit of luck.]
It might be an unsolvable problem, because of too many different things crammed under skills. For stuff like moving silently past the guard, climbing out of danger, swimming across a river, walking a narrow ledge etc. where everybody must succeed, you get into the problem that you don't want a huge disparity between characters, otherwise what is trivial for some is nearly impossible for others (this happened easily in 3e where you could have more than a 20 difference at high levels, was mitigated in 4e with auto-progression of skill bonuses, and mitigated again in 5e with bounded accuracy). But then for other skills a large disparity is beneficial, and that's presumably why they introduced Expertise.