College, lessons learned with first born child

Our son is smart. He scored well on the PSAT in 10th grade. We were getting letters from Ivy League schools, University of Chicago, and a ton of other places. 

Realistically, our son cannot live on his own and needed to be a commuter. Thankfully, he got a large award package which makes going to the local private school affordable. He'd been waiting all summer for his HS transcripts to be received only to be told he also needs the corresponding college transcripts from his CCP classes sent. 

The kid has enough classes from AP and CCP to be a sophomore, but he currently has a dumb schedule. He's been waiting since early June to fix his schedule. He'd contacted the college a few times about his transcripts. We finally figured they got lost or never sent. His HS advisors are on vacation until August so we contacted the secretaries and principal. I, by chance, thought of the community college transcripts as a means to get the ball rolling so we paid $5 and ordered them sent to his college.

I'm not sure with whom to be most annoyed. Seems his HS advisor never sent his transcripts, so that has been the biggest holdup, but now the college transcripts need an authorization form completed to be released. We had ordered both transcripts a week ago, but the college asked for authorization 3 days afterward (and they already billed the CC). Since the college received the HS transcripts, certain people thought the college transcripts were moot point, so we never bothered authorization process until after our son got around to asking his college advisor about how to go about fixing his fall schedule.

If he had communicated with his college advisor sooner, my son wouldn't have to be running around right now.

Weird situation. Live and learn.