Great question Jeff, and thanks for asking.
Generally we are of the opinion that you should routinely update your plugins and WordPress version to the latest version possible.
However, sometimes this can introduce issues that are not always easy to spot.
Case in point, recently a client was doing the correct thing and keeping their WordPress website updated, but ran into an annoying issue where the latest Caldera Forms was no longer allowing people to click the submit button.
If something has been working well, and then stops for no apparent reason, you generally look for a recent update to either the WordPress core or a plugin that has introduced the issue.
After a bit of digging, we discovered this was the case, and then had to revert back to an older version of Caldera Forms to fix the problem.
In a case like this, the only thing you can do is message the plugin builders either directly or via their github repository if they have one, and explain the issue in as much depth as you can and hope they release a patch or fix.
One of the big things with WordPress and WordPress plugins is that it can often be the case that other plugins or pre made themes are causing the issue, so it can be harder to narrow down and fix.
It can also be that a particular plugin version will work fine on one site, and on another site, it will have issues.
The only answer is to test and test again and backup regularly.
If you notice strange issues on your WordPress site, why not get in touch with us and let us see how we can assist.