Update 2020-08-28: Auto-updates for plugins and themes is now built into WP 5.5 and later.
The vast majority of hacked WordPress sites were compromised due to outdated plugins, themes, or WP core. I need to keep my site updated. But should I update manually, or automatically? If I choose automatic, updates will be more timely but there is always a small chance that an update will break something. If I update manually, I can make a full site backup first, and restore if anything breaks – but I am at more risk of a hack occurring in between my manual updates.

I use a checklist to remind myself of the various tasks to perform during periodic WP site maintenance. For me monthly seems about right for these tasks. A very active site would benefit from more frequent maintenance.
My #1 most important WP security and maintenance practice: Always have an up-to-date backup, stored off my site. If I irreparably mess up my site, or it gets hacked in spite of 