In constructing any monitoring system to maximize student progress or remedy lack of progress, I think that it's incumbent for teachers to understand their own environment. This might include professional setting, district expectations, or even school concerns. Certainly, what is given here can be used freely, but it is important that local solutions are crafted with a local sensibility.
I think that the success of an monitoring system has to include feedback and input from students and their parents. I don't think a system can be as effective unless it takes input from all three parties in order to form a solution or progress monitoring tool that the student and their parents can "buy into" in order to be successful. This might involve a conference or a meeting to introduce it, and I think that greater success can result with this in mind.
I would suggest that the use of an assignment notebook or homework book where assignments are written could be a very good starting point. The monitoring system consists of the student writing their assignment for the evening in the book, the teacher then initialing or signing the book indicating that the assignment has been written effectively in it. The parents then sign off when they see the assignment finished or when they see the assignment has been attempted. If there are difficulties, the parents can write notes back in the book to the teacher and a dialogue through the assignment notebook can ensue. If the teacher does not see signatures of parents in the assignment notebook, the breakdown in communication becomes evident. If the parents do not see teacher's signature, the breakdown in communication becomes evident. The purpose of this monitoring system is to ensure that students take responsibility for writing down assignments and show this to teacher and parents. The student can see the signatures, indicating that they recognize everyone is there to support them and there is "no way out." This monitoring system also enables teacher, student, and parent to be on the same page regarding overcoming the challenges with assignments.