Well as ffar as Debian, you could g about upgrading it in many ways. Starting over from scratch may prove to be a lot of necissary work, as I'm not sure what errors you're getting when you boot the kernel. What options do you have specified in your kernel.config? One thing you can try is to have generic stuff compiled in. i know for a fact that 2.6.6 works fine here under Fedora if that helps.
