I don't think Ruby's a bad language, but unless you've built some very good programming habits, it's really easy to get "too clever" with Ruby metaprogramming and do something that's conceptually neat, but makes everyone else who works with you want to strangle you.
I left Ruby behind last year to program Go full time. It's much easier for me to not have to do the mental gymnastics of figuring out where a Ruby method came from.
How hard do you think a Go app would be for a medium-large sized web app? I wanted to write a payment processing website in Go, but I'm hesitant to start using that language.