This year I switched to Ruby on Rails after years of doing mostly Java. I'm quite happy with it, but by far the biggest pain point has been Ruby's dependence on

This year I switched to Ruby on Rails after years of doing mostly Java. I'm quite happy with it, but by far the biggest pain point has been Ruby's dependence on native code libraries. Dealing with CLASSPATHs and Maven was never fun, but it sure beats trying to maintain a working set of Ruby gems, many of which have cascading dependencies on C++ compilers, Python interpreters, SSL libraries, Javascript runtimes, etc.