So, after troubleshooting likewise for 5 hours trying to figure out why likewise wasn't starting lwiod, I find out that Debian 6 changed from "update-rc.d" to "innserv". Why is this important? Well, that means all of those wonderful custom scripts I created in the /etc/init.d/ directory now because "broken" due to lack of what I later came to learn as LSB Headers.
LSB Headers are those commented out lines at the start of a script I never realised actually DID something... Go figure, another dimension of comments to work as code... More information: http://wiki.debian.org/LSBInitScripts
From uninstalling the app, to troubleshooting package installation (dpkg, aptitude, apt-get), to ripping logs apart and googling strings, to specific words, to blind clicking, I finally found the LSB header line mentioning insserv. I should have clued in to it originally seeing it was on EVERY line of the error when trying to start the app.
Moral to this story: Linux apps often add the app name to the start of logs, so don't just research errors hoping for specific errors. Research the keyword, then the terms, and THEN the errors. You'll learn more about the programs, and then you can learn about the debugging.
My brain hurts.