Here's my suggestions:
- make a breaking change to the gem versioning system to force all library, framework and gem authors to use versions properly. If you make a breaking change in your API, you MUST change the major number. Rails made a couple of breaking changes in the transition from 2.3.5 to 2.3.6, for Pete's sake, and a huge number of breaking changes in any of their 'minor number' upgrades. Many gems are even worse. Yes, this is going to cause massive version number inflation. So what? Chrome increments their major number even faster and with less reason.
- If a change to a plugin breaks on an older version of Rails, tell the authors so they can update their gemspec so that other users of older versions of Rails don't get the update.
- Make it easier to contribute to the documentation. It's already pretty easy, but make it easier. Add an "edit this page" link on every documentation page that goes to the corresponding "edit this file" in the docrails project in github.
- 90% of the "documentation" for Rails can be found randomly scattered across the internet on blog posts. Of course, these are usually out of date. "Encourage" (with a stick, perhaps) people to stop doing this and instead to add to the documentation. If that's not appropriate, stack overflow or some other blessed site. Not a random blog post that's never going to get updated and will probably disappear in a few years.