I just wanted to make a few comments on this one for clarity with regard to my procedures. First I would very rarely set different DC for different PC. I generally assume that PC are capable of attempting to do "adventuring things", The deviations in my game generally occur when looking for lore, trying to recall something they once knew or might have heard of, examining an exotic engine and it is less about a singular pass/fail state as it is about how high up the DC ladder you can get and what you (with your specific background might know.)
I think the fundamental wellspring of disagreement here is that some DMs (myself, for one) think of ability check DCs as the difficulty that an indeterminate character would have performing the task. And it turns out that other DMs (Maxperson and UngainlyTitan, for two, if I understand them correctly) think of ability check DCs as determined relative to the particular character who wishes to perform the task.
That's an enormous difference in DMing procedure, one that I hadn't realized existed until tonight. And it will affect everything that has to do with ability checks.
With that procedure, it's not a question of whether "a player" gets to roll; it's always a question of whether this player gets to roll. And moreover, it's not even a question of how hard the task "is," it's always a question of how hard the task is for this PC. Five party members could all climb the same rope, and they could have five different DCs for the task.
I can't imagine DMing that way, or playing that way (though if the DM were quiet enough about it, I guess I might never even suspect it, until the day when PC 2's lower roll succeeds on a task where PC 1's higher roll has failed!).
But I have to admit I can find nothing whatsoever in the 2014 rules that would prohibit it—not only because the 2014 rules give DMs practically infinite latitude for making rulings, but also because they give rather little guidance on how to set a DC for an ability check in the first place.