"I have a moderately complex Rails app that I want to upgrade, but I don't have much confidence in my tests, I maybe don't have proper separation of concerns, and I just know that one hacky thing I did a while back is going to bite me in the ass."
It's just something that happens over time in any moderately complex app. I see Rails point release candidates as a good reminder to bust out rcov and spend a few days plugging up the gaps in test coverage before the stable release comes out.
If you've been procrastinating upgrading your Rails 2.3.x app to 3.0.x, you're really gonna have fun going straight from 2.3.x to 3.1. Sometimes you just gotta rip off the band-aid.