Heh, it's funny. I've been watching a live play from Viva La Dirt League (NPC D&D - it's a guilty pleasure, sue me). These are four players that know virtually nothing about D&D. Total newbies. As in, need to be repeatedly told which die is the d8 and which is the d4 - that level of newbie.
Yet, when the DM runs a 5e adapted version of a skill challenge, there's zero confusion and lots of immersion. He's done it more than once in the series, and every time it comes up, the players get right on board with it and have no real issues.
So, I'm finding that this idea that skill challenges are this bizarre thing that no one could ever understand to be rather overblown. DM says something along the lines of "Here's the situation, what are you going to do to help resolve that problem?" Players make their cases, and roll their dice, and the situation is resolved. No gaming the system to any large extent, very engaged players, and a ton of fun around the table.
But, because it has 4e cooties on it, we cannot talk about skill challenges seriously without all and sundry coming out of the woodwork to question every single statement and bog the conversation down under a mountain of whatabout's and theorycrafting.
For those who might be interested, check out episodes 99-100 of Viva La Dirt League's NPC D&D series for a fantastic example of how skill challenges (or group skill checks in 5e parlance) work.