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Over on his blog, Miguel Guhlin asks:

Anyone have suggestions on how to respond to this question? I welcome all brainstorming ideas...

We are ready to implement a student portal (with teacher and parent portals to follow) for our 1:1 campuses. We would like for this portal to be a web-based, searchable, "pretty"

While "pretty" is subjective, this is one place where spending a little time with either an ID or a graphic designer, or both, will benefit your site. "Pretty" has a frequently overlooked cousin, "Usability" -- sorting out your navigational structures (done in Drupal using the core block and menu items), and making sure your theme enhances these architectural decisions, will often get you both Pretty and Usable, which is a winning combination. Starting with a solid base theme, like Zen, helps you theme your site in a time-efficient way, particularly if you and your team are learning how to design/theme in Drupal. Drupal can be themed pretty effectively via css alone; if you have someone on staff who can work in php, there really isn't much you can't do. Also, if there is one element you decide to outsource, the theme is a pretty good choice.