Enrico said in live-cd-on-removable-disk:
Mostly it boils down to running the xorg-creation script at every boot time.
Well, Enrico, a tool I really grew fond of, which auto-configures X on Debian systems is xdebconfigurator, it lacks being auto-run on each system start, which I consider a feature on normal systems, but for your proposed usage (i.e. a portable USB-storage based Debian system), it would certainly be the right thing.
Essentially, it never failed on me. Except for VMware virtual machines, where all it did wrong was that it proposed too high resolutions which resulted from my dual-screen Windows setup I ran VMware on. You might want to give it a try.