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 been a while but I think the tv shows Leverage, and to a lesser extent, Burn Notice, had quite a bit of this.