Sorry, man, you missed the point again. Windows Update only updates Windows and few other things. Apt (and a few others like it) updates the OS and everything else you have installed. My "Pale by Comparison" remark is more than accurate, as there is nothing even possible of being comparable in the Windows world. Not a criticism, just a point of fact.
Perhaps my loving Linux comment wasn't quite accurate, however. I am in awe of it. Not meritless, blind adoration as you suppose. I am utterly amazed by the resources that come in even your most basic distro. It's amazing how many Windows applications can be replaced by simple shell scripts.
If you count machines and time spent working on a particular OS, I am primarily a Windows admin. My disgust with Windows is rooted in fact. Documented by the hour, machine, and problem.
I'm glad you tried Debian. Not the most polished distro, but for some reason my personal favorite. Maybe you should try Suse or Mandrake until you get your feet wet. Any Windows admin would feel comfortable with them, they have pretty good gui admin features from what I have seen.
Anyway, keep at it, you will eventually see what everyone likes about Linux.