You shouldn't necessarily be compiling ruby on your server anyways you should be using a package (rpm, deb) to install it. Especially if you are losing $500k because you decided to compile ruby on your production server.
One of the challenges of running a production application based on Ruby is the fact that relying on distro packages will fail miserably. Rubygems, in particular, does not work well with distro installed Ruby interpreters.
Ah, I re-read your comment in an entirely different light now, and I agree that packaging your own deps is a great way to avoid surprises when you roll your infrastructure.
