Each kid is so different that I don't want anything I say to be taken as any kind of actual advice, just varying perspectives.
When I skipped first, I think I was challenged for about 2 weeks before I had essentially caught up and wasn't challenged anymore and I don't happen to think I am nearly as gifted as many of the kids represented on this board. I think for most HG+ kids a single skip is just a drop in the bucket. You are simply not going to meet their academic needs without more. Socially those skips may be also getting them closer to their intellectual and social peers, but it may instaed be getting them further out of synch with their peers. This depends a lot on personality. And the in synch/out of synch question may not become clear until the classmates are in puberty.
We have not skipped DS, but we have done combinations of subject acceleration and differentiation. For us, the goal has been to have one or two areas where he is truly challenged and several areas where he coasts and no areas where he is truly bored. Usually we take the areas where he is truly bored and target them for acceleration and let the other areas ride. Even at 13, he is still a child and needs lots of play time, lots of time with his friends, plenty of day-dreaming, lots of out-door free play and time to pursue his own projects (right now a novel for NaNoWriMo). We also insist on music lessons/practice and a certain amount of family learning (reading books together, educational travel etc) If we challenged him in all areas at the levels he his capable of, he would have very little free time to pursue the things he loves.
So I guess the short answer is that we are not looking for him to be fully challenged in every academic area. We are looking for balance with opportunities for challenge, social engagement, relaxation, and family time.
I hope this helps.