Some notes in random order:

I agree that installing the binary wrappers, or symlinks, to
/usr/local/bin, so that they are in $PATH, is a good thing.

The install / install / uninstall problem you mention is a gem problem.
I think that it should be solved at the rubygem side, not specifically
for Debian. That's over-engineered. Have you talked to the gems
developers about that? Maybe you could implement a solution directly in
rubygems.

> I've also implemented a rubygems package that follows the mechanisms used for 
> the ruby package, ie it installs
> rubygems1.8. That means that other packages (eg passenger) can just depend 
> upon the default version of gems
> as they can ruby.

Please check what has been done in Debian recently with the rubygems and
ruby1.9 packages. How rubygems is managed changed a bit. See source
packages: libgems-ruby >= 1.2.0-1 and ruby1.9 >= 1.9.0.1-5. (ie, the
versions in intrepid, not hardy).

-- 
Add rubygems bin to PATH
https://bugs.launchpad.net/bugs/145267
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