Okay so, I gotta ask, because he'll absolutely do this.

So if you're caught stealing, you're executed. Death doesn't matter, and you wake up next time loop like no time passed, with memory of your previous loop, and NPCs go through the motions without memory of the previous loop. Items on your body are still on your body next loop.

Could you steal an item, get caught, adjust your plan for next time until it works? Could you also potentially case and map out buildings of interest in the same manner if they're on the more difficult side to explore freely?