Question: "What was the biggest ‘Why didn’t he just...?’ moment in the series?"
Andrew's Answer: You Only Live Twice... Bond... Blofeld... gun pointed... there is a noise... Blofeld scurries away. He could have killed Bond in 4/100th of a second, but he didn't? What? Why? How? I'm also wondering why they did the whole Rube Goldberg thing with giving Tiffany Case the diamonds at Circus Circus in Diamonds Are Forever. I guess the CIA gets bored sometimes. Just give her the diamonds.
Scott's Answer: I bet you're expecting an answer involving a villain making a bad choice, but nope! Maybe because it's freshest in my mind but in Skyfall, Bond takes M to his childhood home (the titular Skyfall) in Scotland where they EXPECT the bad guys to find them. Do they bring additional weapons? Vehicles? Troops? Nope. They go all Home Alone, planting booby traps and other such mayhem. So I am forced to ask, "Why didn't he just bring more weapons or call in the Marines?!" (Seriously, Skyfall is an extremely well-shot, well-edited, and well-acted movie, but the script definitely has holes in it.)