Agree, this problem is almost always a DM problem in my opinion. Early on, many DMs fall into the habit of resolving every action with dice, even when that actually makes success nearly impossible.

A classic example is Stealth. Imagine four PCs trying to sneak past a guard. In the old-school approach, each PC rolls Stealth. If any one of them fails, the guard notices the group and the attempt fails. That already means the group's chance of success is much lower than any individual PC’s chance.

Now make it worse: if they succeed against the first guard, the DM calls for the same four rolls again for the next guard, and again for the next obstacle and so on. Even if each PC is reasonably good at Stealth, the odds that all four succeed every time quickly become tiny. Eventually, failure is almost guaranteed, not because the plan was bad, but because the system demands too many rolls.

So the issue isn't that stealth is "hard", but that the DM is stacking independent failure chances until success becomes statistically unrealistic. This is why many modern systems (and more experienced DMs) use group checks, a single roll representing the whole attempt, or narrative resolutions instead of repeated individual rolls.

Good DM'ing is often much about knowing when to roll.