I have been happy with https://github.com/lukas2511/letsencrypt.sh. I am trying to get it packaged for Debian/Ubuntu and either get it into Debian-proper or at least host the repo myself to make it easier to use for the common case. Since nginx reloads the cert on a SIGHUP it makes it really easy to have zero downtime renews.

As for getting notified if something goes wrong I use the following in my crontab:

    10 5 * * *  root    test -e /usr/local/bin/letsencrypt.sh && /usr/local/bin/letsencrypt.sh -c > /dev/null

letsencrypt.sh outputs errors to stderr, so any errors will be sent to the root account. To get that working, do:

    apt-get install postfix
    echo 'postmaster:     root' > /etc/aliases
    echo 'root:           [email protected]' >> /etc/aliases
    newaliases

Problem solved.