Even with the help of multiple snapshots, I still haven’t figured out the exact order or things I need to do to upgrade my woody VM to sarge.
I tried first upgrading the kernel, which made the vmware tools stuff break. You have to install kernel-image, grub, as well as kernel-headers and gcc3.3.
Perhaps my mistake was to try to update the bottom levels of the system first. Next time I will start with the top of the stack, and update apache and mysql before I touch the kernel and friends.