We don't talk about Pun-Pun
I suppose you see that as a feature. Perhaps I'm alone in thinking otherwise in this case. If I want to climb a tree, all I need is the DM to either say "yes" or give me a DC. They might add complications, but the default is "you make check, you climb tree".Rather, the game is designed so that the players can't assert control over how a situation is presented to them. Stealth is just a particularly salient example.
If you want to recall some bit of trivia about the magus Quimby (say, for example, that he was an infamous epicurean), you ask the DM to say if you can, and they either say "sure" or give you a DC. The default here is the same, "you make check, you know stuff".
And this is how most every other ability check works. But with Stealth, we have a bunch of additional hoops to jump through. Do you have adequate cover/concealment? Does the enemy have stealth resistance (ala special senses)? How fast are you moving? How far away from your party are you? You can't have a light source, so how do you see?
This strikes me as all very counterproductive. I understand that most people don't want players just entering "stealth mode" (as I recall there was a playtest package which had a set DC to start hiding, which could then be challenged by others, and a lot of people griped that it made stealth "too easy") and lurking about. But there reaches a point where we are demanding far more to perform this task than other tasks, and is the juice worth the squeeze?
I mean, by default, the rules don't ask the Fighter if he's maintained his sword lately, how well balanced his sword is, the length of the hilt, whether the pommel is wrapped in wire or sharkskin, if he has appropriate hand gear (gauntlets, gloves), what stance he's taking, and whether or not his sword is appropriate for his surroundings (is the tunnel too narrow to swing effectively? Will he have to thrust? Can he thrust if his weapon only does slashing damage? Is his opponent left handed? Is the sun to his back?).
No, the character (assuming they are in range) makes a check to see if they hit or not.
Some might say "well, the DM can always grant advantage/disadvantage if they care about such things" but I'm simply pointing out, by default, the game doesn't care about it- it's assumed the Fighter knows his business.
But with a Rogue (or anyone else) trying to use Stealth, suddenly now the game says "hold up, buddy" and is very cautious about whether or not the character can even attempt the task, and has several additional built-in complications beyond simply setting a DC and ruling if the circumstances are advantageous or not.