Drupal updates can be very different. Some of them -- easy patches that you just roll out and forget. Some of them -- break your site. Tricky part is you never know how updates will behave on your site until you actually tried them out.
This is why it is very tricky to give estimates to clients how long it is going to take. They usually do not appreciate answer 1 to 20 hours depending on some random facts.
In this way rolling out updates got delayed and delayed. And then we get to situations after half a year or a year that we know for sure site will be broken after updates. And now hero time begins.
Would it be nice if site would tell you not only the fact that it needs updates but also if it is going to break or not after rolling them out.
Nowadays, thanks to Pantheon's multidev, it is technically possible to automate checking how your updates will behave on the site.
Main idea is to regularly check updates (using drush command) then if updates are found create a separate environment and roll updates there. Afterward to ensure that they didn't break the site (at least visually) we could run some visual regression testing. So in result we have way more predictable answer about "how much efforts it will take to roll updates out".
Here is a full article tutorial about how to set it up http://docs.diffy.website/tutorials/put-your-sites-updates-on-autopilot-with-pantheon-multidev-and-visual-testing.
For sure fixing smaller updates is much easier than fixing big break after year of delays.
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