Note: I am not a developer of GoCD, I'm just a consultant who helps customers with GoCD.
Also, given the nature of fixes and changes - especially security fixes and defects, there can be important changes due to which you would want to upgrade.
In general the upgrades work between nearby releases, though there isn't much of release testing across a year. You end up needing to upgrade between an annual release at least (i.e. 16.x to 17.x, 17.x to 18.x, 18.x to 19.x, 19.x to 20.5, 20.6 to 21.x, etc).
Currently, I'm helping a client upgrade from 16.x through 23.3.0 (likely to be bumped to 23.4.0).
For my current client, we're moving them from self-managed PostgreSQL to RDS, and moving the artifacts from on-disk to EFS. Our upgrades are via Ansible playbooks. This gives us the ability to use a safe DB snapshot (turn off GoCD to quiesce everything) for testing an upgrade. This would give our client the ability to upgrade regularly within a few weeks of a GoCD release.
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