OK, this is a great discussion. I do want to address the OP briefly first
While I agree- binary checks are very meh- one thing about RPGs is that many people play them for role-playing, not combat.
And if you are a speech master/charisma overloader/diplomat/grifter/etc, your tongue is your weapon. You slay foes with it, you plea.. er, charm women with it. You persuade people to take your way. It's ok to circumvent combat by using your tongue. That's what role-playing IS. But - and here we get to the important part - it shouldn't be a 'one button check/select right dialogue/win'.
So ideally (and I know, resources are a problem) what the dialogue-based gameplay would do:
1. Present lore. Many RPGs do this, but many do not. If you're a speech master, game needs to dump (optional) lore on you, new dialogue options, information, etc. To a diplomat, dialogues should matter hundred times more than for a warrior. People should have much more to say and conversations should be longer just because you're a master of speech.
2. Present INDIRECT ways and HINTS as to circumvent a problem, not solve the problem by just having a check. This is something RPGs can learn from adventure games. Hypothetical problem: you need to steal valuable item X from museum/mansion/whatever. Your choices are stealth/guns/speech. If you choose speech, don't just have janitor steal it and give it to you if you pass the check. No, if you're a master of speech, the janitor should, after some convincing/persuading/flattering dialogue, blurt out that there's this thing in this [secret?] room that disables most of security around item X. You still may run into guards, but your problem is much easier than before because an extra layer of security is gone, and that's great because your stealth/guns arent that good. And, you found a real, alternative way to solve a problem, explore (this thing that disables security otherwise you wont know what to do with) all after extracting information from the janitor due to your speech mastery.
3. Don't show successful/unsuccessful checks or that a choice is by default a 'speech choice'. Yes, this will lead to some save scumming, but people who roleplay will be much more engaged. Also, don't have strictly positive options. Have some of these options fail once in a while. Have some of these options don't have effect. Every grifter fails once in a while. Have these options have delayed, not immediate impact. Have NPCs agree with your persuasion externally only to think internally you're too pushy/sly and then fuck you over in the end. People do that in real life. Have real consequences of you being a women charmer, in that men who lust for these women, would hate your guts.
Yes, I know, this is a bit naive/unrealistic, but imagine such a game. A lot of people who love adventure games (like me, for example) a lot of time play RPGs as speech masters/diplomats because we enjoy dialogue and witty/charismatic characters. I would pay a ton for such games to be made where you aren't winning simply by gaining stats and clicking it when it's available in dialogue.