I don't have experience with a skip, but without a skip until too late (I did post-secondary enrollment for my entire senior year of high school, so I went to college one year early and was young with a late summer birthday). I never had to study, so I never learned to study. When things got a little challenging in college, I chose easier courses, thinking I must not really be smart, and all those past As and test scores were just flukes or due to the fact that I was "good at taking tests." I really didn't realize I was very gifted, even though I was in some GT pullouts in grade school, until I read Deborah Ruf's book "Left Behind" (now "5 Levels of Gifted").
In elem, I remember not raising my hand to answer questions even though I thought I knew the answer because I noticed that no one else in the class was raising their hand, so I must not really have the right answer. Kind of a backwards situation - I thought I was like everyone else, so I must not know the answer either. I finally did raise my hand in grad school, because it was part of the grade, but I still figured I was going to be wrong. My never learning to study followed me to grad school, where I was did the same thing I always had done - cram the night before an exam.
As for the social piece, I didn't make any "soulmate" type friends until I was 17, and they were older than me. Although a different perspective since I'm a girl, I did date young and dated older guys, but that was even before I went to college. I turned out OK.
I fit in just fine a year early at college, and I wished that the post-secondary enrollment option had come around earlier because I would have jumped at it in earlier high school grades too (I participated in the first year it was offered). Is PSEO an option in your state (dual enrollment in high school/local colleges)? It was a free program in our state.
My husband was the youngest in his class with a fall birthday, and he actually didn't like being the youngest because of sports. But he was also very underchallenged throughout school. And he didn't have a growth spurt until he was 18 and out of high school, so it wouldn't have made any difference if he had skipped; he was the smallest without a skip too.
Because of all our bad experience with school, we tried to avoid it with our son, and he has essentially been skipped twice. He skipped first in our local school district, which didn't turn out to be enough, so we now drive him 45 miles to a GT school that is working a year ahead. He recently told someone who asked him if he was going into 2nd grade next year, "No, I skipped first and then transferred to a really hard school." And he said it in an excited voice, not a complaining one. I still worry about whether we did the right thing, but clearly he's fitting in better academically and socially than he did before.
Good luck! I think it's great that everyone is supportive of the skip.