[jeffnappi]

This has been my experience. I've been working on a large Rails project that started on Rails 4 beta in ~2014. Since then it's been incredibly stable and the upgrade paths have been quite simple from 4.0 to 4.1, then 4.2 and now we're on 5.0 with a few minor updates left before moving to 5.1.

Everything would have worked fine if we didn't keep things up to date, but just about everything in the software world needs to be continuously updated due to security updates/patches, etc.