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If you liked Gokusen add

...then you might like Great Teacher Onizuka add

Teachers who are members of a gang that wanted to change their life for good, they help those stubborn teenager students who are going to the wrong path & lead them to the right path.

If you liked Kore ga Watashi no Goshujinsama add

...then you might like Hayate no Gotoku! add

Same problem of the main character having an insanely big debt to their masters, both of them are somewhat in love to their masters, their masters are so rich & lives in an insanely large mansion.