Assigning Grades

Now that EM is a high school student, possibly enrolling in PHAA's diploma program, I feel obligated to grade his work. Until now I only graded his spelling tests. He also received grades when doing quizzes and tests in the Thinkwell math courses he took. Now I need to assign a grade for all of his subjects that will be on a transcript. Receiving grades makes our homeschooling environment a little different than usual.

In the past when EM completed work, if there were mistakes, we would work together to figure out why he got something wrong, then he would make corrections, or have additional assignments, until he understood whatever concept was being taught. Now things feel more final when he completes an assignment. I know we can still redo work that he has trouble understanding, but it just feels different. For example, last week he completed a lesson in grammar with a worksheet/quiz that I wanted to grade. He had problems with the assignment, with quite a few errors. Because of that, I assigned an online activity, covering some core concepts that would help him understand what he did wrong with the first assignment. He completed the online work perfectly. Now as a teacher in a traditional setting, I wouldn't change anything about that initial graded assignment. As a homeschooling mom, I want to reward him for figuring it out and give him a better grade.

What is the correct way to handle this?

I can see that a traditional teacher would have far too many students to customize their learning and allow them to work towards mastery in the same way that I can with my one child. It's just not feasible. But shouldn't I take advantage of my special circumstances and allow that? Is that somehow cheating the system? Does grading school work really show us how a student is doing? Does it encourage students to work harder? Learn more?

I guess it would be a good idea for me to figure all of that out before I grade any more work from EM. I'll add that to my list of things to do when we get home from our eclipse trip. I'll tell you all about it next week!