Skill challenges are basically (crappy IMO) proto-clocks. The VP subsystem in PF2 is clunky compared to Blades in the Dark, but it’s actually clocks (more or less). In Blades in the Dark, you might create a clock appropriate to the escape (e.g., a 4 segment clock for “trying to escape”) and then work your way towards that goal. Complicating factors are handled via the dice mechanic, which is the only gap PF2’s implementation has compared to BitD.
To work around it, you’d probably want to set up competing VP thresholds. You’d have one threshold for “trying to escape” (e.g., maybe 12 points) and another (4 points) that fills up when people roll less than success to represent coming complications. You’d just keep resetting the second clock every time it fills, and you’ve injected an appropriate complication into the escape.
This approach works really well in BitD games, which is why I think Paizo should develop it and use it more in Pathfinder. One could get rid of a lot of the bespoke subsystems and replace them with clocks, which would be an actual innovation in the D&D space.