what version of ray are you using?
in the latest version of ray an aborted rake task should cause ray to
disable the extension and stop any further actions, including
restarting your server. if you're using the latest version of ray and
it didn't handle some error i'll be sure to take a look specifically
at the twitter extension to see where i'm failing to catch errors.
the latest version also includes basic support to let authors declare
their extension's dependency on other extensions and/or gems. i tried
to provide patches to as many extensions as i could find who would
benefit from this but obviously missed some, including the twitter
extension. there is a page on the ray wiki describing how to declare
dependencies[1], providing patches to authors of the extensions you
use should be simple enough.
beyond the existing error handling and giving authors a way to tell
ray what their dependencies are there isn't much more i can do.
determining the extension requirements based solely on inspecting the
extension's source code would be far too much effort and probably not
very effective.
p.s. activesupport should be in the version of rails bundled with
radiant, so complaints about that being missing are very strange.
[1]: http://wiki.github.com/johnmuhl/radiant-ray-extension/extension-dependencies