I’m a sucker for slow and meticulous planning and organization in film and games despite being messy and disorganized in real life. Like 80% of the appeal of Stalker and Tarkov to me is having to deal with the bullshit inventory system, some of the early Rainbow Six games seem interesting because you plan much of the siege beforehand, and XCOM where you have to improvise when the plan inevitably fails.
Some related shows that I’m fond of in no order:
- Early seasons of Breaking Bad
- Season 1 of Prison Break
- Money Heist (Spanish version)
- Better Call Saul (the scams and loopholes)
It's not a movie but if you like games with this vibe, Hitman World of Assassination's Freelancer mode. It's a roguelike mode where instead of just going after a set target with certain set ways of taking em out, you get random NPC targets with a random patrol, so it's half planning for how you might want to take them out, and half improvising when you realize there's no easy options or you wander into the wrong place