During a grammar lesson in the class the teacher asked the students how they would make the name Biggs possessive. My son held up his hand and told her he would add an apostrophe--Biggs'--and she said that was wrong, that it should be Biggs's.
The teacher is correct. I used the same style as your son for many years but decided to make the switch after more indepth research on the topic. While the 's style is incorrect it is used so commonly that to many people it looks right, but many experts would prefer s's. This is a great example of the value of taking classes. It is a wonderful thing to be exposed to different ideas and different ways of doing things.
Perhaps the experience of the class will improve your son's endurance or give him more motivation to work on his handwriting. When the main issue is endurance practice will lead to improvements. Ultimately I believe it would help him more to independence and self confidence if he could have the chance to take the class on his own. Giving him space would show him you have confidence in him and it would allow him to find ways to advocate for himself. It may be helpful to look to the future. If you hope he will be able to go to college without you at age 18, he needs to start taking the steps to get there. Being able to take a short homeschool class at the age of 12 is a step on that path.