Chasing upgrades
If you wanted to, you could probably be upgrading some part of your software systems every week.
I don't recommend it. Here's why:
God bless them, the open-source community is constantly working to improve CiviCRM, your Drupal or WordPress CMS, your plugins, your CiviCRM extensions.
And every time you do an upgrade, you've got things to think about:
Back up everything, and be sure your back up restoration process works.
Some level of sanity testing to be sure your upgrade didn't break anything obvious.
Some level of finger-crossing to hope it didn't break anything not so obvious.
Some potential for downtime during the upgrade, or afterwards if anything didn't go as planned.
Changes to features, configuration, and processes that you may already be familiar with but will need to adjust for. These aren't always documented or obvious.
So what to do?
Here's what I recommend:
Upgrade only when you have a good reason — typically this means you have reason to believe that the upgrade will give you a feature or bug-fix you need, or it's a security update.
If you can, consider upgrading to something less than the very latest release. All software has bugs. A version that's been around a month or two without subsequent bug-fix releases is likely to have been vetted by the community a little more thoroughly than the version that came out yesterday.
Remember, you don't get points for having the shiniest new software.
But you do get a lot of points for having you reliable systems that let you do your work smoothly.
All the best,
A.