Some parents and students perceived demanding homework assignments as a frequent source of grievance, particularly for those high performing students who want spare time for independent study and cultivation of talents through extracurricular activities. Teachers tended to perceive homework assignments as a meaningful extension of instruction time and a media of communication between school and home. Cognizant of the possible conflicts about homework practices between school and home, the current study investigated homework issues from the students' and their parents' perspective while maintaining the integrity and information provided by the teachers of those students. The overarching goal of the current study was to establish a conceptual and applicable model for evaluating homework practices in local schools. Data collected included student and parent surveys, teacher homework philosophies, sample homework assignments, and homework hallway charts. The survey results were analyzed inductively and six key issues were identified pertinent to homework assignments in a well performing middle school in a Mid-western state in the United States of America. The six prominent factors identified include: grade-level homework coordination, positive perception about homework, homework as academically engaged time, motivation of doing homework, uniqueness of math homework, and ability-matching of homework. Some implications for parents and educators were articulated.