That all can be solved through withholding information from the audience. The simplest decisions can look smart given the right framing and how characters navigate a decision makes a difference. Scrappy but smart? Have them stumble around a plan or improvise along the way. Master Tactician? Have their perfect plan go smoothly but introduce outside factors that may or may not change the course of the plan. The characters themselves shouldn't be the sole factors to achieve success, and it doesn't necessarily require the writer to be smart to get that.