Robert, why are you back to Outlook? I know you dabbled with using Mac OS X as your primary OS, but that must not have stuck if you're finding yourself in Outlook for email / task management. Having switched to the Mac myself, I can honestly say that I'm glad to be rid of Outlook - it's seductive in that it seems to have everything that is needed in one app, but for me that's also its biggest downfall; I could never get Outlook to perform fast enough to keep up with my thought processes (and I'm certainly no brainiac as my family and friends will be quick to point out).
Elliot - kudos! This is a great WP primer, and I love that you recommend Kubrick. One question: I see that you recommend both breadcrumbs and "pretty links". I can't seem to get the breadcrumbs plugin to work on my site, and from what I've read it's due to an incompatibility with pretty links. How did you get around that?