My brother has to get up early to read the newspaper since enrolled in high
school.
これは三人称で、sinceは、副詞で、
それ以来～という意味で原則現在完了形のhaveと使うたぶんあってると思います
Answers
My brother has got up early to read the newspaper since i entered high schoolです
ありがとうございます！！！
My brother has been getting up early to read newspaper since he entered high school. です
ほんとにありがとうございます！！！助かりました！！！
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ありがとうございます！！！