Clojure has (roughly the equivalent) of problem #1. Java has a lot of, err, great libraries, I guess but many of them are, sadly, hidden behind a Java-esque API. To use them from Clojure you will need to spend time wrapping up the Java-esque nature of the API into something more Clojure-like and unfortunately the answer to the question "How do I do X in Clojure" is often "Use Java library Y." Thankfully Clojure's Java interop is relatively painless.

Personally I spent a long time in the Java world and then migrated to Python and Ruby. I was shocked at how easy to use many libraries are in the Python world. Libraries like Feedzirra, Mechanize, Python Twitter Tools and so on don't really have equivalents with respect to ease of use in the Java world.