I have some doubts about Ruby's enterprise readiness after a recent experience in attempting to provide a fix to what I thought was a bug in the Ruby supplied core routines. I was experimenting with Ruby and RoR when I found a problem in the date parsing routines, and after a quick look at the source code I thought that I could probably solve the problem fairly easily.
The date parsing routines (as you can imagine) are reasonably complex and support quite a range of date formats, and before making the change I looked around for the unit tests for the routines - without luck. Since I was flush with the excitement of working with a new language and in a community-spirited frame of mind I asked for a spec for the routine in order to write some test cases, again without any luck.
This seemed like some fairly elementary and important pieces to be missing from what should be a fairly fundamental part of the core routines, and it made me concerned about the readiness of the organisation surrounding Ruby to scale up to the level that was needed if the language was to truly take off in the way you've forecast here.
Having said that, the fact that I felt confident enough to even attempt to hack some of the core libraries after only a week or two of working with the language speaks volumes about the ease of use and natural feel of the language. I also was extremely impressed by the fact that my very first post to comp.lang.ruby was answered by Matz himself (how many people have had posts on Java groups answered by James Gosling recently ?)
I sincerely hope that the sorts of gaps that I found here get plugged as soon as possible so that the language is able to robustly withstand the sorts of challenges that I know are going to be thrown at it in the next year or so.