Thanks everyone! DS5 is in all day pre-k. Here they do not have half day pre-k or k. So the time in a classroom environment won't be an issue. He will also know some kids already in k this year that will be in 1st next. He's shy, but not around kids and not when he finds something interesting or challenging. AND I figure worse case scenario is it's NOT good for him to move him up, and we hold him back to be with the kids he's with now.
He actually LOVES to sit down and WORK rather than play outside or games, etc. So the desk thing won't be an issue for him either. He's quite mature for his age, even though he has his "definitely still a 5 year old" moments from time to time. I honestly think that he is on a 2nd grade level (at least 3rd for reading), but I would never push that far b/c I think he would be lost socially, etc.
DD3 could easily be in the pre-k class this coming year, but she has the late bday as well. While socially she would be fine skipping ahead, she is no where near as advanced as DS5 was at her age. So even though she would be capable, the boredom factor won't be as big of an issue as it is with DS5.