I've never run a BitD game before, so I'm trying to get a good idea of how many obstacles (and how difficult) to throw at a newly formed crew. The score in mind right now is sneaking in and stealing a unique security key from the Amber Knights, a Tier 2 gang, while they're distracted by fighting/hunting down the ReCyclers, a Tier 1 monocycle gang the crew has allied with. Argon Entertainment, a Tier 4 organization, has turned the local gang warfare into a spectator sport with the Amber Knights as the local favorite. The major players of both gangs will be in the arena, having their battle televised.
Obstacles that come to mind:
Getting to the Knights' HQ, which probably involves avoiding monocycle patrols and traversing the dense neighborhood without attracting attention from sympathetic locals.
Getting past the HQ's security: Locks, sensors, patrolling Process.
Danger clock - ReCyclers' stand: The ReCyclers can put up a good fight, but they can only drag out the competition so long. Whichever side wins the arena match, the Knights are probably going to be on guard after the game ends.