"Always, what kind of ~"
"always" 「いつも」
"what kind of ~" 「どんな内容の〜」
"Always thinking of what kind of video to make."
「いつもどんな内容の動画を作るか頭を悩ませている」
"thinking of ~" の代わりに "racking their brains for ~" 「頭を悩ませている」
"Always racking their brains for what kind of video to make"
「いつもどんな内容の動画を作るか頭を悩ませている」
He's always scratching his head trying to figure out what kind of video he wants to create.
この場合、次のような言い方ができますよ。
ーHe's always scratching his head trying to figure out what kind of video he wants to create.
「彼はいつもどのような内容の動画を作ろうかと頭を悩ませている」
to scratch one's head で「頭を悩ませる」
what kind of video he wants to create で「どのような動画を作りたいか」
ご参考まで!