This article from SaM‑Solutions describes a practical, step‑by‑step migration path from Umbraco 14 to Umbraco 16, with a brief look ahead to Umbraco 17 and the .NET 10 upgrade.

The authors explain that the jump from Umbraco 13 to 14 is the most disruptive, while upgrades from 14 to 15, 16, and onward become progressively smoother as major breaking changes are already behind you.

The main message is that incremental, well‑prepared upgrades are far less painful than skipping multiple versions at once, and that investing early in tooling, automation, and editor modernization makes future Umbraco migrations significantly easier.

https://sam-solutions.com/blog/umbraco-14-to-17-upgrade/