I had the same experience as you and OP, doing an RoR implementation from the operations end was a tangled mess of gems with various mangled dependencies onto one another, with those dependencies being to certain badly documented or undocumented version numbers.
Also, when I did this implementation several years ago, the core RoR and gems documentation web pages were a mish-mash of broken links.
These problems drew me to reading the blog postings of the mongrel gem creator, to try to figure out how to get mongrel interacting with the other gems properly. The blog did not exactly inspire my confidence in the software.
In fact, the project went over budget and over deadline. It is the project which went most off the rails, so to speak, in my 2+ years at that company - even more than the attempt to implement Sharepoint. The outside developers thought they would "save time" by doing it all in RoR, but they failed to deliver a production ready system. I know that Twitter made a great effort to pull itself off its initial RoR base, and that it is widely said that RoR is not scalable. It is possible it will straighten out over time, I remember back when Java application servers were slow resource hogs with poor frameworks. My initial experience with RoR has left a sour taste in my mouth. Maybe the operations background of this person has significance - it may look OK from the developer standpoint, but the production operations end needs a lot of work.