It's best to pick a project and try to build it, rather than learn things from the outside. In isolation, Ruby can be annoying to learn because it's syntactic sugar seems unnecessary. In context of an app, though, it's great. The sugar makes sense.

Rails has a bit of a learning curve, but that learning curve is well rationalized. To borrow a Steve Jobs-ism: you're starting on the 10th floor, when everyone else is starting on the 2nd floor. Out of the box, you get a killer asset pipeline and complete MVC system that's standardized and conventional.

You can throw together a well built webapp without cutting corners in a fraction of the time doing it by hand. Things like a solid REST API practically come free with Rails. That's really valuable.