Veronica, I think he might wind up doing exactly that, with the backpack and compression straps.

As for a smaller laptop: we both use Dell Inspirons (his is a 700, mine is a 710) and they are teeny weeny. They don't get much teeny-weenier. He doesn't carry his every day but he's a computer science major, not to mention a database programmer/consultant, so he needs it several days a week.

The pannier didn't work out so well today; he couldn't carry the laptop and he said the pannier was awkward off the bike. He has a separate bag for the laptop -- one of the TimBuk2 sleeves that has its own shoulder strap -- so he can carry that separately, but then he's hauling two bags around all day.

This is why people drive cars, isn't it? (Not an option for him, there is no parking on campus.) I can carry my laptop, whatever work I brought home with me, and extra clothes for days when the a/c is crazy at work, all in a medium sized TimBuk2 bag ... but I can leave it all in my office all day.

Anyway. Thanks for the suggestions! I will pass your thoughts along. And thank my lucky stars that I am not in school anymore.