The thing that struck me the most at the time was scaffolding. In the original Rails demo they essentially said, "make me a todo list" and poof, there it was. All you had to do was customize two snippets. It really was amazing.
By Rails 2, they were already saying you shouldn't be using scaffolding. I had sort of realized that scaffolding "wouldn't scale," to misuse the expression; by your second or third app you usually didn't bother with it, instead generating a migration and a model and doing the rest by hand.
I wasn't using Java prior to Rails, but I am using Java now and I would say the essentially disparity between the two at the outset was simply maintenance. Rails didn't have a past to worry about back then. My impression is that it still does a lousy job of handling upgrades—though at least with bundler et. al. they have finally achieved a semblance of stability. I suppose I should be able to check out code written 9 months ago and arrive at a working Rails app. There was a time during Rails 1 and 2 when you experienced real fear that running "gem install" might hose something, or that on a new machine the gems you needed might not even be "out there" on the internet to be installed. Java still goes further on these fronts, and probably always will, since "corporate" technologies will always be about retaining as much of the investment as possible.