A crew of highly specialized scoundrels -- safecrackers, intelligence gatherers, muscle for when things go wrong. Anyone could be the high charisma con man. Bonus points for the crew being a bunch of misfits brought to gether to do a particular job.
Reaction rolls for pulling cons.
"High tech" (high arcane, of course) security measures.
Equally "high tech" (high arcane) ways to create distractions and fool those security measures.
An emphasis on (player) cleverness to circumvent obstacles.
Ocean's 11. The Italian Job. The Great Muppet Caper.
D&D can handle a fantasy world version of these kinds of stories. While megadungeons and wilderness exploration are well regarded classic approaches to D&D (and megadungeons can be very heist-like), the rules are pretty well set up for a game about big heists and capers.
Because D&D actually treats 10 minute game turns as a meaningful unit of gameplay, there is solid mechanical support for infiltrations and time sensitive B&E jobs. Many thief skills can be attempted multiple times with no penalty, but it it could be ruled that it takes time to do them. Maybe one turn passes for each Open Locks check or Find/Remove Traps check, and on a failed roll, you can choose whether to take another shot or whether time is running out and it's time to cut and run. Meanwhile, the wizard has is keeping a zone of silence around the safe cracker -- but that has a fixed duration too. Elsewhere in the compound, another party thief and the fighter stand ready to stage a distraction, drawing attention away from the vault where the "Eye of Vecna" is sealed up.
Patrols can be modelled with encounter checks, with patrol frequency matched to the frequency of these checks. Maybe the default frequency is once every third turn, but it increases to once per turn if an alert is sounded. When encounters do happen, the rules tell us the distance at which the encounter starts (2d6 x10 feet). And if our adventurous thieves get the drop on the guards (the results of the surprise check show that the guards are surprised, but the PCs aren't), then the rules already note that the party can simply slip away and avoid the encounter (Moldvay, B23). Close call. But the job is still on. But woe be it to the party if the guards catch them by surprise.
This just scratches the surface of the idea, and the more I think about it, the more I like it. It's the basic approach we're taking with the Rainy City campaign, where high stakes capers can be set up by the PCs independently, or on commission from city wizards out to steal from or sabotage their rivals. The ruins of the great school of magic lie beneath the waves, a megadungeon delve for adventurers willing to take those kinds of risks. But other kinds of high stakes jobs abound in a city this full of the treasures of a previous age, as well. The rewards are great for teams with the skill and panache to pull off the robberies.