I must say I'm impressed with Debian so far. It still has not convinced me to drop Gentoo and start using Debian, Gentoo is simply too cool for that.
With both distro's it's always a bit iggy what will happen if you do emerge world or apt-get upgrade respectively. Most of the times things go well and you have an up-to-date system. Sometimes things go wrong.
Like with Debian a while back. After an upgrade the network refuses to work. No IP address, nothing. I could bring it up with ifconfig, route and dhclient, but all manually. The first two commands were scriptable in rc.local as a work-around, but the DHCP request did somehow not work.
Cause? The line
had disappeared from /etc/network/interfaces. The only lines for eth0 looked like:
iface eth0 inet dhcp
Strange how that could happen, it was kind of annoying to find out.