CentOS - Dec 2004 - Remote Installation

I "upgraded" a server from RH9 to CentOS remotely, as from WBEL 3.0 to
CentOS 3.0, and a RH8 to CentOS 3.0..

Used YUM to do it..

HOWEVER, it was (basically) Redhat - > Redhat (based) upgrade.

I have no idea how well it would work to do a Deb box that way.  

Maybe build a local box (or VMWare image, that way you can use the
Snapshot to recover screwups), with Deb on it and try the "upgrade" ..
See if it bombs out.