My son attended a very small private school for 6th and 8th grades--you may be able to see where this is going...
He skipped 5th on entry, but over the summer beforehand, the school realized that the 6th grade class was too small to be functional, so they combined it with the 7th grade. My son made friends with the 7th graders and did all 7th grade work (except in math where he was doing Algebra I).
So the next year it made sense for him to move up to 8th grade. Which meant that he was double skipped--something that we had never intended going into it.
He decided to return to homeschooling at the end of 8th grade, and now, two years later, he's decided to try the local public high school as a 9th grader.
We'll see how that works out.