I finally got around to making the site look decent. I went ahead and found a theme that looked pretty good as a base, hacked around with it until I got it to look how I wanted, then added multiple sidebar support the way I like it. In the process of checking out WordPress 2.6 compatible themes I stumbled across an interesting super minimalistic theme that was used as the base in a design contest. If I ever get the urge to do a design from almost scratch it looks like it would be an excellent starting point.
So, what do ya think? Look good?