Momofthree,
We just went through this. In mid-January we put our 8 yr old son into 2nd grade.
First,

. For me this was a really difficult decision. I loved hs'g. My son loved it also. I NEEDED to put him in school. I was going to college myself and taking really hard classes. We unschooled last year but this year started following the Classical Method (which requires a lot of work on my part).
My son is also very social. He now loves going to school. He has made tons of friends and is excelling academically.
There are problems though. We are sending him to a private Christian school. This required some conformity on his part. The first three weeks were rough. Then he started to get into the swing of things.
I would just say that sending a child to school is just different. You pick your problems either way. They are just different problems. Homeschooling isn't perfect and neither is sending them to school. They both have their pro's and con's.
My best advise would be: Take is year by year. If it doesn't work out for you, you can always bring him home. And there is no harm in that.
Maybe the school you are looking at would let him go for a half-day or maybe just an hour. Can you pick who his teacher will be? Can you meet with him/her ahead of time to see if they will be a "match"?
Best of luck to you in whatever you decide.
