Continuity mistake: In the scene where the whole gang is eating at the soda shop, everybody starts leaving. Doody is in the back, in the middle, on the railing. He's getting ready to leave, takes a bite of his ice cream and sets it down. In the next shot, he sets it down again.
Visible crew/equipment: In the scene during the American bandstand, at the end of the song when the teacher is dancing in front of the band members, the crews can be seen. The dressing and the hair doesn't match Grease era at all, and someone is sitting on a director's chair as well. (01:06:20)
Continuity mistake: After Danny has knocked over a hurdle, we see him getting up; however, the Hurdle has either moved and stood itself back up or it's disappeared completely. In the next shot it has returned to its fallen position.
Answer: Well, Danny was out of town, at the beach. It's quite possible that the rest of T-Birds didn't live close enough to each other to see each other during the summer. Also, they may have all had jobs, or been travelling with their families. It's also possible that they DID see each other, although maybe not as "T-Birds". When they saw each other on the first day of school, though, they were Seniors, and they were ready and excited to be T-Bird seniors.
BGraz
Another possible reason is that not all of them were allowed to see friends during the summer. I had a couple of classmates whose parents were strict about them focusing on schoolwork and/or getting a job. No phone calls or visiting friends on the weekends or during summer: "You can see your friends at school."
Do you really think any of the T-Birds had strict parents?
People quite often rebel against strict parents.
When they asked Kenickie where he was, he said "working, which is more than I can say for any of youse kids" suggesting that the 3 stooges (pun intended for their stupid routine that prompts Danny to tell them to "be cool") didn't work all summer. Also, Sonny needed to borrow money in the dinner until he could get his allowance.
In regards to not living close enough to each other, it is worth mentioning that having access to a vehicle was much less common compared to nowadays.
KeyZOid