I knew for a long time that rails is somewhat fun to work with. The first time I read something about it, I went to check it out, and kindof liked the idea. Web development really isn't my cup of tea, so I didn't do anything with rails; but really, the idea made somewhat sense to me.
It's unfortunate that the implementation is such a piece of crap. Luckily I don't have to deal with it firsthand, but the stories I hear and read everywhere speak for themselves. I won't enumerate them all; but in case you're not familiar with them, the Debian Ruby team has a pretty clear explanation on their website. In addition to complaints by packagers, I also hear that many ruby developers recommend that you install gems inside the project you're running (or that you ship your software in such a way that it includes those libraries as part of your source). Oh, the horror.
Now, in theory, to update to the latest version of RubyGems, you just need to run
sudo gem update --system
But - depending on what version of RubyGems you have installed, running that command may lie and tell you that you have nothing to update. If you’re currently on RubyGems 1.1 or 1.2, you need to run a different set of commands to update RubyGems:
sudo gem install rubygems-update
Seriously. This is why we have distributions, packagers, and, really, people spending a whole shitload of time making sure everything works together nicely. This is why there is Debian, RedHat, CentOS, Mandrake, SuSE, and whatever.
Me touching rails? Not with a 10-foot pole. Not if you pay me a million, in any currency. Stay away from my system!