I’m glad to report that my PowerBook migration w/ OS X’s built in was both uneventful, and by and large successful (hooked up, went outside to kick some hackysack, came back and viola, 36GB transferred). The only things I’ve had to reinstall so far:

• Cisco VPN software (w/ Kernel extensions, to be expected)
• Quicksilver (strange, but it worked after that)
• GnuPG – my SSH and GPG keys looked like they moved over fine though
• Transfer doesn’t copy the /Library/WebServer/Documents if you use the built in Apache
• Developer Tools needed to be reinstalled
• Printers were not carried over

Besides that, things look hunky-dory. My bookmarks are there, my licenses seem to work, all my Keychains need to update but are otherwise a-okay. Good job Apple!

(Updated: I’ll be adding more caveats and non-transferred items as I notice them)