Angular releases twice a year with a documented deprecation policy and automated migrations. The upgrade cost is genuinely low if you pay it on schedule.

Why teams fall behind

Not difficulty — priority. An upgrade has no visible output, so it loses to every feature. Then a security advisory arrives, or a library drops support, and the upgrade becomes urgent at exactly the moment it is largest.

Keeping it boring

• Put it in the sprint after each release, permanently. It is maintenance, not a decision to be re-litigated twice a year.
• Run ng update and read what the schematics changed rather than skimming past them. The migrations are the documentation.
• Track which dependencies gate you. Usually two libraries determine when you can move, and knowing which ones lets you watch their releases instead of discovering the problem mid-upgrade.
• Upgrade one major at a time. Skipping versions skips migrations, and the automated path is most of the value.