I love programming RoR, but in my limited use I have run up against roadblocks that say Ruby and RoR are not mature enough yet for my shop. It is coming, but it isn't there yet.
Examples:
1. Between Ruby 1.8.2 and 1.8.3 the behavior of undefining constants that had not been defined changed. This broke the version of ActiveRecord that instiwiki depends on (making the three step install a 7 step install if you don't count looking all over the internet for why "step 2 - run the application" was failing. The RUBY behavior changed in a manner that broke a core library.
2. ActiveRecord uses two slightly different idioms for handling primary keys. One idiom handles non-numeric primary keys well, the other idiom does not. The net result is that for most operations you can use ActiveRecord with legacy or distributed systems, but some operations fail. Before I get flamed, submitting the dozen or so lines of code fixes for review/approval/inclusion are number 8 on my priority list.
3. ActiveRecord dynamically generates SQL on every call, imposing the overhead of the prepare phase of the query on every call to the database. This seriously limits the scalability and performance of the platform, since in a single SQL call up to 80% of the resources used may be used during the prepare phase, before any of the work that the statement does is actually performed.
In contrast, a prepared statement imposes that overhead once on the first call, and thereafter only the resources used in the actual work of the statement are used. When you're on the heftiest hardware available and it's already maxed out, this is not just a stumbling block, its a serious barrier.
For what its worth, I do not feel that programming in Java is quite as bad as you seem to. Programming to EJB is that bad, and it is sad that the java world has become so bloated that we now have an acronym for plain old java objects (POJO). But let's not blame the failings of clunky frameworks on the language.
Now that Sun is officially supporting JRuby, it will not be long before your server guy will have no say in the matter because a ruby app, to him, will be a java app. Hang on, and work it into a small place first. It will grow.