Atashinchi no Danshi (2009)

They are similar by:
-one female help a lot in the boys' lives
- similar feel: lots of comedy with a lot of heart.
- she goes through lengths to help the boys she comes to care for.
-There is hinted of romance, but there isn't much (veeeeeeerrrrrry small).
-the female leads do learn from the boys just as much as she helps them.

Difference:
-The female in Gokusen is a teacher while in AND, she is the boys' step-mom.
- The female lead in AND was hesitant at first before accepting them while in Gokusen, she was accepting from the start.

Due to family circumstances, high school student Miko Sonoda is forced to live at her uncle's boarding house. However, before she can arrive there, Miko is already met with a bad omen: while trying to find the place, she suspects that someone is following her! When her uncle comes to her rescue, the assumed stalker happens to be one of his tenants, leaving Miko embarrassed on her first day.

Miko learns that she will be living with five unique adults, including the accused man. Additionally, it turns out that he is Jun Matsunaga, a 29-year-old designer who seems to lose his temper easily. Having made such a humiliating first impression, Miko believes that only a miserable life awaits her. But in the presence of Jun, she comes to realize that living with adults is not so difficult after all—and there may even be enough room for romance.

both the fls are homeless and end up living with the ml who is rich. they’re also both similar in the sense that the fl is older (in atashi no danshi she acts like a mother to some of the boys she lives with) and she earns their respect in the end

Its got the basic storyline of girl finds herself suddenly rich after being poor. Nothing is like what she expects it to be and she finds herself in some pretty interesting situations.