Go run doen the eve online stories. People have gone under cover in enemy groups for years, just to rise in the ranks until they can just plunder the whole org for the equivalent of tens, even hundreds of thousands of dollars.

I think there was even a guild in the game the specialized on long con espionage called like "the crimson rose" or some such.

The game itself is basically excel, but the "player generated" environment is an epic story generator.