This is a very thorough, albeit not necessary accurate, story of one's experience using Java.
I agree that there are TONS of duplicated effort out there:
Tapestry, Struts 1/2, JSF, Wicket, etc are all "MVC _and_ Component Oriented".
Hibernate vs JPA (yes, I know Hibernate is JPA 2 compliant, and yes, I know JPA 2 has less features).
XML processors. Java common utilities, the list goes on.
But these days there seems to be a quite select few of winners in my book: Google Guava, JUnit (TestNG is neat, but JUnit is good enough for 80% cases), GWT, Spring Framework or Java EE6 (your choice, or mixed).
Java based ORMs can't beat dynamic language ORMs in terms of "it's fun to use" (or less setup). Period. But having said that, Java based ORMs took different approach compare to ActiveRecord or Django Model. Java based ORMs are more similar to Ruby DataMapper; they required a little bit of setups (have to define your own model, etc) but in the long run, I think these second concept (or known as the Data Mapper pattern: http://martinfowler.com/eaaCatalog/dataMapper.html) may have been a better choice. Of course that is for the long run... not weekend project, get-prototype, get-funded, and get rich-quick scheme.
Java-based App Servers are heavy but with a caveat, depending on your loads, Java-based App Servers may use less resources (or degrade gracefully) because they are utilizing thread vs bringing up Rails + Ruby process per request.
When it comes to dev-time that depends on your experience. For example: I use JUnit, Eclipse, and JUnit plugin as faux-REPL. No re-compilation needed. Setting up the tools I mentioned is done via Maven + vanilla Eclipse. In another word: don't get too gung-ho with the number of tools I mentioned. It's fairly simple to get it to work.
I do have to say this though: as much as people hate Maven, there's no better and more complete build/dependency management/project management tools in other ecosystems (Ruby, Python, Lisp, Haskell) compare to Maven. None.
When it comes to IDE, I love the shortcut navigation keys of my IDE, Eclipse. I'm contemplating to purchase RubyMine in the future as well because quite frankly I can't live with VIM/Emacs. NetBeans has a decent Ruby IDE for a while until Oracle decided not to invest in Ruby anymore. Not sure what the stats these days. I need my "press X to go to Class/Method definition" to read the actual source code.
Yes, Java has been slow moving forward under SUN. Things have changed under Oracle. They're pushing it aggressively and toward the right direction.
People keep saying that the "WAR" deployment is one of the best thing that happened in Java. I heard Oracle is preparing Java EE7 that supports multi-tenant architecture.