This implies that asking a friend or relative is not a thing that your character would do. Which goes back to my remark about thin settings and unconnected characters. Because for a normal human being with the normal degree of social connection, no one can write all that into a character background prepared in advance.In my case, if I can drop things into fiction, I start thinking about what I'd like to drop into fiction next instead of what my character would do.
When I play my character in Burning Wheel, I only ever think about what my character would do. This includes looking out for friends, relatives, fellow members of his order, etc. And that "looking out" is resolved via Circles checks. In 4e D&D that could be a Streetwise check, or a raw CHA check. In 5e D&D that could be a CHA check ("Find the best person to talk to for news, rumors, and gossip") or even WIS ("Get a gut feeling about what course of action to follow"). Or of course, the GM could decide that no check is required - freeform negotiation around when checks are or are not required seems a pretty standard feature of 5e D&D.
I don't see the different between your first two disjuncts - in a game of D&D, how would you "find a ladder in a convenient spot" without mediation via the GM?Instead of checking the area (via DM ask) for a ladder to get over the wall, I just find a ladder in the convenient spot. Instead of wracking my characters memory (via DM ask) if I know someone who might be able to heal us for free in this strange town, I'm just related to Nurse Joy, and every town has one of those.
As to the second one, we have a fundamental difference of sensibility: for me, the idea that I would experience my PCs' memory and sentiments by asking another person to tell me what I'm thinking is completely at odds with inhabitation of my character.