I skipped the Rails 3 upgrade just simply because I couldn't justify the time sink. rspec made it ridiculously worse with the difference in Rails support between 1.x and 2.x. I'm guessing with Rails 3.1 coming out I'll have to upgrade just because most of the plugins I use have moved on and don't backport bugfixes.
It'd be nice to evolve an app without having to constantly wasting time on version compatibility. It's an absolute nightmare if you have any non-trivial-sized app.