One of the things I like about Unix for tools like this is the ability to pretty much set it and forget it.
But sometimes it needs a little steering to make sure it can manage itself, so I thought it would be interesting to start a thread so we could share the tasks you set for your Pi-Hole so that it can look after itself with minimal interaction.
Hopefully this will help share ideas for us that like to tinker under the hood a bit.
I'll start with my pihole [RPi 2B]
/etc/crontab Nothing spectacular, but a wee bit of customisation in there
# Weekly Backup Rotation
0 4 1 * * root tar czf /bup/backup1.tar.gz /bin /boot /etc /home /opt /root /run /sbin > /dev/null 2>1&
0 4 7 * * root tar czf /bup/backup2.tar.gz /bin /boot /etc /home /opt /root /run /sbin > /dev/null 2>1&
0 4 13 * * root tar czf /bup/backup3.tar.gz /bin /boot /etc /home /opt /root /run /sbin > /dev/null 2>1&
0 4 19 * * root tar czf /bup/backup4.tar.gz /bin /boot /etc /home /opt /root /run /sbin > /dev/null 2>1&
0 4 25 * * root tar czf /bup/backup5.tar.gz /bin /boot /etc /home /opt /root /run /sbin > /dev/null 2>1&
#
# Monday Morning Updates
0 5 * * 1 root apt-get update && apt-get upgrade -y && apt-get autoremove && apt-get autoclean
20 5 * * 1 root /usr/local/bin/pihole -up > /dev/null 2>1&
30 5 * * 1 root /sbin/reboot
#
# AM/PM Gravity Update
0 8,18 * * * root /usr/local/bin/pihole -g > /dev/null 2>1&
#
# Second Level Blacklists
0 7 * * * root cat /etc/pihole/regex.list.standard > /etc/pihole/regex.list && service pihole-FTL restart > /dev/null 2>1&
0 23 * * 1-5 root cat /etc/pihole/regex.list.extra >> /etc/pihole/regex.list && service pihole-FTL restart > /dev/null 2>1&
0 1 * * 1-5 root cat /etc/pihole/regex.list.bed >> /etc/pihole/regex.list && service pihole-FTL restart > /dev/null 2>1&
0 2 * * 6,7 root cat /etc/pihole/regex.list.extra >> /etc/pihole/regex.list && cat /etc/pihole/regex.list.bed >> /etc/pihole/regex.list && service pihole-FTL restart > /dev/null 2>1&