No-win situations are not fun, and are bad game design.
I'm not gonna give you too much shit about the various random encounters-you listened to criticism on a lot of them, and that was decent of you.
The Concrete Forest Apartments and the DMC Bank, though? That's "oh, well, you succeed I guess" leading to "fuck you for playing, enjoy losing access to one area at best and the entire DMC at worst" unless you have an appropriate skill or an item useful exactly one other time in the game to better result. That? That's bad game design. That is not fun-that is a waste of time. The entire point of video games is to enjoy time spent, and time not enjoyed is time squandered.
If there were a way to get literally any useful information out of Caleb beyond something you can learn a dozen other places at the cost of an app used nowhere else in the game, I'd be considerably less mad. Maybe if you could bribe the kid, or get a task that'd mollify him (thus extending playtime) I'd mind less. As it is, though? It's a shaggy dog story. Again, not fun.
I would rather that the Concrete Forest exist soley as a flavor object than have it be impetus for you not being able to return to the DMC for an entire goddamn year. If not two.
I prepared Explosive Runes this morning!