I keep it up-to-date religiously and rarely run into breaking issues, but I have occasionally. I keep an eye on the release notes (https://rc.home-assistant.io/blog/categories/release-notes/), so I usually have at least a week's notice when a breaking change is coming and can adjust. I used the Met Office integration in some of my automations (setting a fan's speed based on the outside temp) and spotted that it was going to be disabled, and switched to Accuweather before this month's version came out.