I guess, the first question is Python vs Ruby. I use either and don't have a strong view to be honest unless you do so number crunching in which case Python off

I guess, the first question is Python vs Ruby. I use either and don't have a strong view to be honest unless you do so number crunching in which case Python offers more in terms of libraries. As to which webframework to use, RoR is indeed a bit like a fat man but so is Django. If you're new to web dev, I'd say go with something lightweight, ie. web2py or even flask in the Python world or Sinatra in the Ruby world.