Last year I gave Ruby a try (for an ambitious project) and I have to say that it felt like going back in time to my C++ days. The syntax is very, very different and the environment support (command line + sublime) is clearly not something that I have done in the past 10 years.
I like the flexibility of it but coming from statically typed languages I find myself trying to replicate the same way of thinking in Ruby. Which in turn is making me less productive. Given the mental blockage and fear of productivity loss I am not certain I can push through to get to the point of productivity with RoR.
I am giving Python a try next! I would also appreciate any pointers to get me up to speed w/ Python frameworks for web development.
PS: The rails part is just fine, I have developed an Active Record based framework to do web development on C# in 2003. So I am more specifically talking about Ruby the language.