I know Java well, though I'm not primarily a developer. As a DevOps guy, there are a few places where I'd love to be able to write a quick program in Java to take advantage of one API or another, or to ensure compatibility with the app I'm trying to manage or what have you, but between the boilerplate, the classpath, the compilation step, and the awkward command line, it's almost never worth it, and I write it in Ruby or Bash instead.
The complaint about overstrict PKI libraries is spot on as well. Dealing with Java's PKI infrastructure for https URLs, etc, in a systems level setting where, you know what, sometimes the CN on the cert ain't gonna match the internal name, is a huge pain. Other languages are actually pretty bad about this too, and so too often I resort to calling out to curl -k because it'll just shut up and do what needs to be done.
It's clear that this is all because Java is built around the assumption that you're creating a big program and you're going to use an IDE and you're willing to deal with multiple steps before you have something that'll run on the server. That's fine and dandy. If the Java community wants Java to be more useful for smaller tasks, then Tim's complaints here are dead on target. But if not, I long ago gave up trying to use Java in this way, and I think Tim should do the same.