AI is a new kind of bulk tool, you need to know how to use it well and context management is a huge part of it. For that 1-1 example, you would do a for loop with new context with subagents or a literal for loop for example to prevent the 'first two and last one' issue. Then with those 1-1 summaries, look at that to make the determination for example.

Humanity has gotten amazing results from unreliable stochastic processes, managing humans in organizations is an example of that. It's ok if something new is not completely deterministic to still be incredibly useful.