"His father's a pilot so he'll be able to become one easy."
"His dad's a pilot so he's a shoo-in."
"His father's a pilot so he'll be able to become one easy."
"father's" => "father is"
"His father's a pilot" 「父親がパイロット」
"~ so ~" 「〜なので〜」
"he'll" => "he will"
"he'll be able to become one easy" 「彼はパイロットになりやすい」
"His dad's a pilot so he's a shoo-in."
"he's a shoo-in" 「彼は絶対パイロットになれる」
"shoo-in" は「必ずできる」や「必ず勝つ」という意味です。
His father was a pilot so it's easy for him to want to become a pilot.
「父親がパイロットなので彼はパイロットになりやすい」は英語で「His father was a pilot so it's easy for him to want to become a pilot.」と言います。「~しやすい」という形は英語で「it's easy to ~」です。親と同じ道を歩む行為は「following in their footsteps」(足跡を従う)と言います。
父親がパイロットなので彼はパイロットになりやすいけど、試験を合格するのはわからないです。
His father was a pilot so it's easy for him to want to become a pilot, but he might not be able to pass the test.