Felisa, Fang of Silverquill

Flying
Mentor (Whenever this creature attacks, put a +1/+1 counter on target attacking creature with lesser power.)
Whenever a nontoken creature you control dies, if it had counters on it, create X tapped 2/1 white and black Inkling creature tokens with flying, where X is the number of counters it had on it.

Boss's Chauffeur

Boss's Chauffeur enters the battlefield with a number of +1/+1 counters on it equal to one plus the number of other creatures you control.
Alliance — Whenever another creature enters the battlefield under your control, put a +1/+1 counter on Boss's Chauffeur.
When Boss's Chauffeur dies, create a 1/1 green and white Citizen creature token for each +1/+1 counter on it.