You're not trying to miss the ground, you're trying to hit the space around it, which is incredibly difficult (one might call it a recreational impossibility). . .
I also think any DM who allows the player to roll for this deserves what he gets.
No, it's actually really important that you fail to hit the ground, instead of succeed at flying. Here's why:
Flying difficulty: Nearly Impossible, DC 30.
Hitting the ground: Very Easy, DC 5.
It is significantly more improbable that you'll succeed on DC 30 than fail a DC 5. At low level, anyway. Ability bonuses and skill proficiency will tilt those scales over time.
And yes, you're right about the DM deserving it
If hitting the ground was actually DC 5, then we would observe character non-magically flying on a routine basis. We don't observe that, therefore it's probably not the case.
The assumption being that characters regularly fling themselves at the ground, and statistically speaking, about 1 in 4 of them are failing at it miserably? Except characters don't regularly fling themselves at the ground.
Or you're assuming that a character who pulled it off would tell other characters, who would then go on to specifically attempt to fly. Or miss the ground. That wouldn't result in routine flying, because the act of telling other characters about it is a Help action, which grants Advantage, which negates the Disadvantage that is sorely needed for the endeavor.
In any case, if a player suggests, "I'd like to throw myself at the ground and miss," and the GM says, "Okay, roll for it," then... that's fine. I don't actually see what that has to do with what resolution system you're working with.
The resolution system tells the GM what to do after "okay roll for it."
In D&D, the character succeeds or fails/makes no progress/makes progress with a setback. The fail means 1) the character failed to hit the ground, 2) makes no progress toward the ground, or 3) hits the ground anyway and probably takes damage too. Two of those outcomes can be considered flying.
Eyes of Nine touched on this - you can fling yourself at the ground in Dungeon World. If you roll too low, the consequence is up to the GM, in her choice of what Move to make, which is significantly different from D&D's three basic choices.
Genesys's narrative dice allow a player to roll Advantages even while Failing, or Threats in the face of Success. So if the player says "I fling myself at the ground," and the GM says "roll for it," there's a phase of dice-interpretation that precludes (from what I can tell) the simple result of, "welp, you failed to hit the ground."
A degrees-of-success system, (maybe White Wolf's add-the-successes?) might not overcome the problem. Pathfinder 2 might fall into this. If you fling yourself at the ground and get a critical success, maybe you hit the ground without taking damage (you found an ergonomic rut to land on). A fail is still a fail, right? What about a critical fail? Does this mean something Extra Bad happens? That could be interesting...so you'd fail to hit the ground - be flying - buuuuut break your noggin in the process?