When starting web development, I found it easier to learn Ruby and the Rails Framework from scratch than to use Java which I had several formal classes in. I think that says something about Java's documentation/community support. Ruby/Rails has railstutorial.org, tryruby.org, rails for zombies/code school, and railscasts. All these high quality beginner resources made using Ruby instead of Java an easy choice. The ot…
It's really that with the exception of Play/Grails/Vert.x the frameworks are horrifically over-engineered by developers who live and breathe in the enterprise space. Nobody has ever really cared much about smaller, more startup land developers. So Java has required so much knowledge and involvement just to do the simplest things.
I would take a look at frameworks like Play for the future of the platform.