Y'all are NOT going to like what I am going to say. I am really really really sorry to have to say it, but if I hadn't seen it with incredible frequency with my own eyes I would NOT say it.
I think it is the way English is being taught in our schools, NOT so much that it is your child/children.
My mom was a college prof who did a LOT with her students, including very in depth feedback on assignments, and she required more out of projects than most of her peers (most profs didn't want to grade so they didn't require as much, esp for intro classes). What her students turned in by the late 90's was about on par with that sample of what you gave us of difficult child 2's writing. These were NOT freshman, they were juniors and seniors if they were in any class she taught. She had a policy that she would grade until the 10th error in spelling, grammar, punctuation, etc... What was SHOCKING was the number of otherwise seemingly smart kids who had to redo the papers. She would give them a week to redo it or they could take whatever grade they had earned by the time she hit the 10th error. There were a couple of people in administration who tried to tell her she was too hard on the kids with this rule!!
I read a lot of the papers, also ones my husband's students turned in. Awful does NOT begin to describe it. Sadly, some of the students from that time are now teachers. Jessie had a 6th grade Lang Arts teacher who couldn't write a letter home to parents. She got very upset when a parent marked a letter to parents with a red pen and gave it to the principal. She was mad the first two times the parent (a friend of mine who was NOT an English major or honors English student) corrected her letters to parents, but she made NO effort to not repeat the mistakes. Sadly, the principal of our middle school sided with her that it was highly inappropriate for a parent to do this (never mind that the parent mailed it to the teacher instead of having their child deliver it in order to save embarrassment of the teacher!) and was quite scathing in a reply to "chastise" the parent!! Sadly for the teacher and principal, they put their replies in writing and the parent went to the SD superintendent and said she would go to the school board AND the newspaper if things didn't change! The teacher was a second year teacher with a minor in English!! NOT in English Literature, in English - which means she took entire classes dedicated to sentence structure and punctuation but still couldn't do it! She actually waved her transcript around to prove she was "qualified", but she barely passed the English classes (NOT the A she had bragged about to the students when they questioned how she graded their use of punctuation!).
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Even scarier are some of the textbooks our kids use. Not only do they often NOT have proper grammar and punctuation, they sometimes have the rules for grammar and punctuation wrong, or their examples will illustrate the wrong way as the right way. Textbooks are a HUGE business, with schools being pushed to buy "newer and better" ones each year. The error rate in these texts keeps going up. The publishers have said that they don't have "time" to fully proof them for errors. I can remember finding maybe 5 errors in my 6th grade science book, mainly because our teacher would have us copy it instead of trying to teach it to us. We had to copy huge chunks word for word. By doing this I picked up on a lot of the errors because my parents were education junkies and I had read textbooks that were quite far ahead of 6th grade by the time I got there. The grammar and punctuation errors drove me up the wall quite literally by that age. I though 5 or 6 errors in a textbook should mean the school ask for their $$ back. These days I would REJOICE over a textbook with 5 or 6 errors as I have seen some with close to that many a page. My dad was on textbook selection committees for a long time for his large SD (one of the largest in the state). Several times he had me read a chapter or three to get my opinion as a student. MOST were just awful, with some of the most outrageous errors I have ever seen, including giving completely wrong definitions for glossary words. Sadly there are very few teachers who ever read a textbook. They operate off of the teacher's guide and the lesson guides and those usually don't catch the mistakes or make the same mistakes as the textbooks.
So not all of this should be put to rest on difficult child's shoulders. A tutor and some testing to see if there is an Learning Disability (LD) or speech issue going on would be an excellent thing. Helping him NOW with this will be a huge help to his future. Does he write his assignments out longhand or does he type them? Can he have an alphasmart to do his classwork, notetaking and assignments on? When we switched to one with Wiz the detail and quality of his writing went up astronomically. For him it was so painful and difficult to write that he just wrote the shortest thing he could, regardless of his knowledge. It also has a spell check and may even have a grammar check. Teach difficult child to use both of these on everything he writes. Make it a game to try to have as few errors as possible - a personal goal or give him a small reward or something. It can make improving his grammar and spelling a goal, rather than keeping him dependent on the grammar and spell check.
I am sorry he is having these problems, but at least he is young enough that you can help him with them. You might also search out games that work with the rules of grammar and punctuation, etc... they won't be as fun as Warcraft or whatever, but maybe for every 15 min he plays a grammar game he gets 20 on the Wii or whatever?