Aruite Ippo!!

The following content is intended for mature audiences and may contain sexual themes, gore, violence and/or strong language. Discretion is advised.

From MangaHelpers:
High-schooler Saionji has moved into a boarding house with a really cute young landlord named Sakura, who also attends his school. Though it's really near the school, the place is pretty broken-down and all the other tenants are strange women. They include little Hana, who wears costumes in public, a sloppy, lazy teacher, and his slightly uncivilized schoolmate Akira. Living in the boarding house does not help Saionji's reputation at school, but he has a huge crush on the landlord. Will he be able to handle living with all these bizarre women, and somehow win Sakura's heart?