Earlier quoted context omitted.
Upgrading from v11 to v16 is not materially different in Postgres from v14 to v16. Same tools. Same strategies.
We are planning to upgrade from 11 to 17 soon. Even thinking about it is giving me ulcers. Our infra provider said we actually need to upgrade to 13 first, and then to 17. They did not provide a reason.
Did a restore to a stage environment, worked on my upgrade scripts until I was happy (deployed to VMs with ansible, so manual work to write the upgradeprocessfor me), restored again and ran the upgrade process fresh, and then tested my application, backup scripts, restores, etc. Had everything working entirely smoothly multiple times before pulling the trigger in production.
No stress at all when we did it in prod.