Ours schools are similar--I guess its the way all US schools are now (totally not how it was when I was a kid and I think this is something that has not been improved on!) You might want to ask if he actually minds being towards the last picked up. My DD actually got upset when I was to early in line to get her. She liked getting to play/talk with her friends while they waited. So I stopped trying. School got out at 2:30, I drove up about 2:40 and just pulled up in a line of about 5 cars. If I got there at 2, I still wasn't first in line, so the other worked out much better for me.
I'm hoping the kids won't mind being last again this year. 2:30 is in the middle of Henry's nap, so I'm planning to go as late as I can to let him sleep. School's new this year, and parking/carpool line is going to be a nightmare in the beginning--I'm betting I can show up at 3:15 and they'll still be getting kids out there, at least the first few weeks.