Is it possible to make rubygem installation a smoother process?

I'll spare you the boring details of trying to get perftools.rb
installed for ruby 1.9 on our Koala today, except to link to this
awesome commit message: "Install ruby_core_source when needed, instead
of yelling at the user"
https://github.com/tmm1/perftools.rb/commit/1ac8143bdc565a1bd8d23d4ffefcd85e3ec6c5d1

However, I'm wondering: the first time you install a gem, is it merely
a matter of

while true
  break if package_installs # You've earned a break
  google(error_message)
  find_missing_dependencies
end

Or is there a better way?

So far, I'm thinking:
* Maybe this is why some people install everything via Debian packages
rather than rubygems
* Are there any web sites where you can look up the thing you're
installing, and find out what roadblocks various people had along the
way? (Apart from google.com)
* Maybe someone could have a virtual computer randomly try to install
various gems and report which ones fail on a clean install

Andrew

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