“The Three Strikes Job” - Does it hold up?

In the mid-to-late 2000s, heist stories were all the rage after the roaring success of Ocean’s Eleven in 2001. Heist stories are great because they lay everything out for the audience, so they know pretty much exactly what to look for, even in a complex scenario. Then something goes wrong, and the audience gets to try to figure out if they can find the way out before the protagonists show them. Generally speaking, they feature a lot of humor in the form of personality conflicts between the different kinds of specialists who all get pulled together to make the heist happen.