motd login message won't save after restart
Solution 1:
Debian has /etc/motd as a symlink to /var/run/motd by default. This is updated at boot by /etc/init.d/bootlogs.
To use your own motd simply break the /etc/motd symlink and create it as a regular file.
Solution 2:
No, after an Dist-upgrade you have the old motd. I think the best way is to use the/etc/motd.tail and you can take some additional informations in it.