Atlassian would encourage you to upgrade on every release, but that's often not practical for several reasons.
You don't want to slip too far behind - the larger the upgrade jump, the more work it is, smaller increments tend to be easier.
Most of the time, you see people upgrading on a 6-12 month frequency though, and that's not a bad pattern to adopt - frequent enough that the upgrades aren't large complicated jumps, but infrequent enough that you're not into planning the next one the day after doing the current one!
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