But I remember specifically using open(url), parsing some HTML, and writing out a CSV. Today there are libraries to make that trivial for an experienced Rubyist, but this was Ruby 1.8.0. FasterCSV was still just around the corner, there was no hpricot yet. And you're working with blocks right out of the gate. The little 40 line program (including whitespace) took me quite awhile. It read (what I thought was) very pretty. But I think the Ruby community tends to take for granted how big a role idiom plays in Ruby. In the early days when you didn't necessarily have access to all that, fighting your way through syntax errors trying to learn the language by referencing the pickaxe was definitely one of the bigger challenges I've faced as a programmer.
By that point I was already very proficient with c#, had written a fair about of VBScript in ASP3. But I really struggled with how opaque learning how to be productive in Ruby felt.
I'm curious how many of your criticisms are reflective of Ruby as of today, rather than the Ruby that upset you when you were starting. I learned Ruby literally eighteen months ago, have never written code against 1.9 to say nothing of 1.8, and everything in this thread is totally foreign to me.
Can you remember any examples? I can't think of very much in plain Ruby that's non-obvious.