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I've only skimmed the other comments so sorry if this is repeating things, but: I strongly feel you should not do a lot to prep for him. Let him handle this himself. He's not a child, and even if he were, it's good parenting to allow a kid to experience failure so they can learn and innovate on their own how to be successful and take responsibility for their own success. In other words, DON'T take it as your own job to do all the pre-packing and putting stuff in the car the night before. After he has done drop-off a few times, he'll figure out on his own that it's easier if he does prep the night before. If you both get into the habit of assuming that you're always going to do all the labor and prep to make parenting as easy as possible for him, then that's the rut you'll be in forever! Let him spread his parenting wings and fly.

In our house, DH is responsible for dropoff of our older daughter, and will be responsible for both kids once DS starts daycare. I don't do anything to prep for him/them. He has figured out what needs to be done and he gets it done. If he doesn't, then he won't get to work on time. Yes, we've had a few failures here and there (like the time we completely missed out on parent-teacher conferences because he failed to notice the sign-up board) but it all works out, and I am so so happy we've set this precedent so in the next 20 years of parenting we'll have the assumption that we are both equally capable and responsible for all parenting duties.

@PawPrints: I second this. We switched our schedule at the start of this year so that DH can do drop-off and I would do pickup, and I am really terrible about not over-engineering things, so I tried to really force myself to step out of his process and it's been working just fine. He gets up at the same time I do (about 2 hours before LO is up), so that he has time for a long shower the way he likes it. I leave at 6:30, LO is up around 7:30, and what happens in between and after that is up to him. The only thing I do is put out clothes for LO the night before because DH admits himself that he has no acumen for clothes selection and Lo doesn't care enough to do it herself yet, but otherwise they're on their own.