Do caster out of combat options matter?

[Amechra]

I think there's maybe a bit of player expectation bias at fault here as well.

Yes, that's the problem. WotC used terms like "Easy" or "Medium" without thinking about who those checks are easy or medium for. Given how simple the skill proficiency system is, I'd argue that it's very reasonable for a player to expect that being proficient in a skill attached to one of their "good" stats means that they're good at doing a thing, not "congrats, you don't screw up Easy tasks like some kind of scrub!".

Like, we can do all kinds of post-facto justification for why the whole thing totally works you guys, but c'mon. It doesn't help that giving people auto-passes on checks for reasons other than "your bonus is so high that rolling a d20 would be a waste of both of our times" is a band-aid. "I've decided that this is a Medium check, but the Barbarian (+7) doesn't have to roll because I've decided that they'd probably succeed" is just admitting that the skill system produces results that the table thinks are implausible.