I've been developing software with .NET professionally for the last five years or so, and aside from the occasional foray into other languages I've more or less specialized in that environment. While merrily hacking away at our back-end here at Semingo, we've recently made the decision to develop an aspect of said back-end in Java. As it's always a good practice to keep an open mind and experiment with other technologies I've happily accepted the challenge.

After working with Java and its associated tools for the past three or so weeks I have several observations to make:

1. The prominent free Java IDE, Eclipse, is actually a very full featured and impressive platform but takes a lot of getting used to. Some of the idioms and concepts are radically different than Visual Studio; for instance, whereas in Visual Studio you'd create an "ASP.NET Application Project", in Eclipse you create (or convert to) a dynamic web project and then add something called facet to your project; for instance, a Dynamic Web Module facet allows you to easily create and debug servlets, and the "Axis2 Web Services Core" facet allows you to create Axis2-based web services and work on them from within your IDE. To actually make use of these features, however, one needs to develop a pretty hefty knowledge base on the various technologies involved (J2EE and servlets, servlet containers like Tomcat, WTP etc.)
   
2. Eclipse is next-to-useless without some tinkering; in particular, what I originally attributed to very immature web development plug-ins - the WTP umbrella project I already mentioned - turned out to be the default memory settings of the Eclipse launcher. The launcher hosts the Java VM and its baseline configuration is simply inadequate. In my case adding the following switches: -vmargs -Xmx512M -XX:MaxPermSize=128M to the command line resolved all of the problems I had with the various WTP plug-ins, as well as the myriad crashes I've experienced with the IDE. In fact it's rock-stable now.
   
3. The Java language has some unexpected caveats; for instance, whereas in C# the designers eschewed fall through in the switch statement (you can group labels to implementations, but you cannot fall through from the implementation of one case statement to the next), the Java designers elected to maintain C-style behavior. I'm of the belief that switch statement fall through is the cause of a huge number of subtle, hard-to-find bugs, and was surprised to learn of this discrepancy between the two languages.
   
4. Enumerations in Java, a relatively new feature added in 1.5, are an impressively diverse feature which is a great deal more powerful than its C# counterpart. I only wish the designers would also allow for a more simplified "SOME_CONSTANT = 3" type syntax, as it's somewhat cumbersome to have to actually use constructors for the purpose. Additionally Java does not (to my knowledge) support implicit conversion operators, which makes necessary constructs such as SomeEnum.CONSTANT_VALUE.getConvertedValue(). It's not a huge issue but it's one of the many areas where syntactic sugar in C# is useful.
   
5. Speaking of syntactic sugar, there're several aspects where Java simply falls short of C#: disposables, iterators and delegates. Yes, I know delegates are an essentially religious issue for the Java designers (mostly for historical reasons, I suspect), and I won't deny that anything you can do with delegates you can do with nested classes, but at ridiculous verbosity. As for disposables, I find that the using keyword in C# is one of the most useful language constructs I've ever encountered, the use of which goes way beyond the original intention of elegantly scoping unmanaged resource use; finally, iterators are tremendously useful and cut a lot of unnecessary boilerplate code out of the equation.
   
6. The Java ecosystem is riddled with code- and buzz-words, to the point of being annoying. If you thought .NET has too many sub-technologies and acronyms, you should try Java. Just to get the taste buds going, here are some of the keywords I've been messing with for the past couple of weeks: J2SE, J2EE, Servlet, Eclipse, WTP, (Apache) Tomcat, Axis2, SAX, JAXP, JAX-RPC, JAR, WAR, AAR, EAR, JDBC, JavaDoc, JSP and JavaBeans. And that's just off the top of my head! To someone with any sort of Java experience this list wouldn't seem intimidating or even exhaustive, but to a new-comer that's simply too much. There is also an import cultural distinction: Visual Studio and its associated technologies (.NET, ASP.NET, ADO.NET etc.) are designed to ease you in as you learn the ropes; I found it much easier to simply start working with them and learn as I go, whereas with the Java counterparts I usually found myself trying to rework code samples found on the 'net while scratching my head.
   Now don't misunderstand me: the Java technologies are generally impressive, mature and usable, but the learning curve is not nearly as comfortable as the competing technologies from Microsoft, and the tools and documentation just aren't as polished.