Not sure if you've ever checked it out, but the seattle.rb meetings on Tuesdays at Vivace on Broadway are usually well attended, and both Aaron Patterson and Eric Hodel are usually there. It's like having a superstar Ruby/Rails team at your fingertips, and everyone is super helpful.
I'm curious as well. While I haven't upgraded any older projects, I started a new project on 3.1.rc4 several weeks ago and (besides deprecation warnings for some testing tools) have had very few problems that grabbing a newer gem couldn't fix.
We usually host a hack night every second thursday in Toronto, and we're going to move it to Sunday for this. If you're interested in attending (or could host people on Saturday), you're more than welcome - http://www.meetup.com/torontoruby/events/25743841/
Lets get involved and squash some bugs!