Once, I did this using Gentoo and its LiveCD. It requires some familiarity with Linux though.
The way you do it, is adapting the LiveCD to have a default-root password (one you choose beforehand) and starting the ssh-server by default. This means extracting / mounting files form the LiveCD's, chrooting into the LiveCD environment, setting the password, unmounting, repackaging / compressing the whole thing and writing it back to an ISO. After the ISO is booted (from CD-ROM or USB) you can install Linux on the harddisk from there. Nice thing is, whenever it doesn't boot anymore, you can put in the 'adapted LiveCD', log in to the LiveCD environment with SSH and troubleshoot from there.
I'm pretty sure it can be done with Debian as well.
It's not that hard, but it requires some fiddling with 'image'-files. Let me know if you want to know more about it, if you're interested I will supply a short HOWTO.