That is indeed interesting stuff, Jeff. It would be interesting how it would work out in a prolonged Red Team exercise--and whether the "immersion" could really display ingrained assumptions and world views enough to make a difference.

Personally, I'm not sure you need to go that far to develop the sort of empathy and understanding required to get inside the opponent's head, nor am I convinced that it can it can adequately accommodate the variety of non-cultural and ideological factors that shape insurgent decision-making. This can often be highly idiosyncratic, shaped by leadership styles, risk tolerance, adaptability, immediate (and highly dynamic) political context, group dynamics, etc. In other words, if I think of all the Islamists or members of armed non-state groups that I've known, they've varied dramatically in terms of attitudes and behaviours (just like, say, Republicans, US military officers, or environmentalists).

The broader issue you're addressing is absolutely vital. I've always thought that the best analysts combine subject knowledge, empathy, common sense, and a degree of imagination that is also firmly based in available evidence. It is not that hard to recognize, in my experience--but I haven't the faintest idea how you would test for it.