A backup before a core update you start
Start a core update from the dashboard and the backup is part of the job: a new one, or the most recent if you took one within the hour. If neither is possible, the update does not start.
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WordPress minor and security releases install themselves, and plugins and themes update on the switches you set. A core update you start from the dashboard takes a new or recent backup first, checks the site still answers, and attempts a restore from that backup if it does not.
At a glance
Start a core update from the dashboard and the backup is part of the job: a new one, or the most recent if you took one within the hour. If neither is possible, the update does not start.
Automatic updates on for the twelve plugins you trust and off for the one that breaks the checkout every March. It is a switch per plugin and per theme, not one setting for the whole site.
Plugin auto-updates are something this market has learned to charge for, usually as the reason to be one plan higher. Here it is a checkbox, on every Pressy.
No. They are included on every Pressy, and there is no plan above yours that unlocks them.
For a core update you start from the dashboard, a backup is taken first and we attempt a restore if the site stops answering. For a release WordPress installed itself, restore any backup from the dashboard; it is free and takes no argument. For plugins, switch automatic updates off for the one that gives you trouble and leave the rest running.
Plugins and themes, yes: each has its own switch. WordPress core always stays on minor and security releases, and you choose whether major versions install on their own or wait for you.
The rest of what people switch for. The whole list is on the features page.
Automatic releases, per-item switches, the backup before a core update you start and the restore attempt after a failed one are all included, at every size.