Things which just won't work with Debian (woody)
1. Automated security updates
Normally, apt-get upgrade can be used to retrieve security updates
in a non-interactive manner. This does however not work with sendmail (which
asks 2 stupid questions which only require the default answers anyway) and
proftp (which uses /dev/tty in its postinst file).
The locales generation is broken when using it the first time. Call
dpkg-reconfigure locales again to fix it.
The boot-floppies don't contain the gdth.o module by default, which is a pity
especially if all servers require it...
The standard version doesn't work on loopback devices, this is fixed now, but
the tool still isn't in the default $PATH of normal users.
5. Apache + SSL
It is not made clear that if people want apache + ssl for consumption by the
general public, they must install apache-ssl, but not libapache-mod-ssl.
The latter doesn't work with some broken browsers.
The standard maximum value of broken connections is way too low. MySQL is
unusable on woody without frequent flush-hosts command invokation.