That's simply wrong. I've maintained a moderately-sized Rails app since 3.x, and updating never took more than an hour or so, even for the major version changes.
It's also deeply unfair to the Rails team. Your timeline should include, as the first entry:
- Rails 1.0 is released, showing the web development community how to structure a project, delivering us from XML, and banishing config.backup.inc.php3 from our nightmares.
Rails came about in a world of SQL embedded in html, or (almost worse) the idiotic idea of "templating languages" that were poorly designed re-implementations of php ("but this time it's just for templates!"). Testing meant clicking through your application, and javascript was exclusively used for replacing the deprecated <marquee>.