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Dylan must face his fear of flying when the Wilsons plan an exciting trip by plane; inspired by the bravery of the Tuskegee Airmen, and with a little help from a dream, Dylan finds the courage to take flight.
When Dylan accidentally signs up for a gift-wrapping competition instead of a rap battle, he must rely on his cousin Rebecca's training and his own rhythmic skills to wrap his way to victory and avoid a year of chores.
When Grandma Viola moves in with the Wilsons, Dylan and Charlie devise a plan to win her back from Rebecca's room but their scheming backfires. Meanwhile, Myles and Yasmine get Bethany to spill the beans on all of Rebecca's secrets.