Cracken fits into the category of pilot that needs to have the squad built around him for maximum synergy. Just like Lando Calrissian before him. This allows squad mates to take a target lock and focus action for example to lay down an accurate attack and at pilot skill 8, there isn't many ships he will not be able to influence.
Cluster Missiles allows Airen to pass on the free action ability twice in a single round because of attacking twice which is a great way to give a massive boost to the combat phase. Guidance Chips as usual to increase the damage of the ordnance.
Keep in mind however it grants a free action, if your squad mate has a stress token, then it won't apply but this can be mitigated with the Wingman EPT. Lastly, Cracken's ability will force you to fly in formation making you vulnerable to builds taking advantage of anti-swarm tactics such as Ruthlessness and Assault Missiles.