If I'm getting set up, I really don't distinguish between Rails itself being irritating and one of its dependencies being a PITA. Those dependencies are part of the architecture of Rails, so it gets the blame. It's not like I need foo version of ruby if I'm just doing some quick scripting.
That's 3 days you could spend curing cancer. Tongue in cheek aside, I use to rage when I had to spend 3 days doing server admin and configuration. Along comes heroku and dotcloud and it's a godsend.
That is, except for Lion and XCode 4.2/4.3, which caused me about three lost days. 'rvm get head' and 'rvm install 1.9.3-head' fixed that, though.