Hi Mia,
Have you considered subject acceleration instead of full skip? He may be ready for 2nd grade in some subjects but not all? It sounds like school is getting too stressful for your kid. I wouldn't worry about his handwritting just yet. He is only five (almost six).
I don't know if this would make you feel better, but I will say it anyway. My dd started 1st grade at 6 yrs 5 months. She was reading at 4/5th grade level but the only thing she could write was her name. We never schooled (homeschool or otherwise)so she never tried. She is now in 2nd grade and her writing is beautiful. She is a great speller and is getting high marks on both presentation and content on book reports.
I guess my point is he may just not be ready for writing at 2nd grade level but he may be ready for math/reading. In a few more months this may not be a problem anymore. Let him take the lead.
I believe wholeheartedly in skips and subject acceleration, but only when the child is ready for it and it won't cause undue stress.
