I've had similar experiences. I've done Win32 and OLE and all that jazz, and then
.NET in its heyday. Although
.NET has evolved, it seems to be falling further behind the JVM ecosystem overall. Here's what I mean by "overall":
1) the JVM itself is extremely battle tested now. There are even viable alternative JVMs. In terms of troubleshooting, reliability and management, the JVM is a non-issue. It's like the sun rising in the morning.
2) The knowledge base of solved problems, libraries, projects and skills for the JVM world dwarfs .NET. Further, it seems that with the exception of a few guys like Brian Beckman, the smartest people in the world have made their choice: they do their work on top of the JVM. If you want to do massive streaming and/or parallel computing, you're going to turn to one or more top level Apache projects running on the JVM.
3) Interestingly, the world of Java.next languages such as Groovy, Scala, Clojure is really getting traction. This is closely tied to #2, the smartest people in the world work in the JVM space. Clojure in particular is very nice, and you can deploy Clojure apps as Java jars, so in a stodgy big company setting, you can actually deliver.
4) Finally, a problem I've seen since with Microsoft over the years (still a problem) is that MS solutions tend to address a problem facing *Microsoft the company* but do not address problems facing *developers and customers*. MS is reactive. When Java began to shake up the scene, MS rushed to market with a "me too" version (the .NET runtime and C#). Same deal with Windows Phone (answer to iOS), Silverlight (answer to Flash), and on and on. Here's the kicker: Microsoft's track record in keeping their promises is not good. If you tied your fortunes to MS tech initiatives in the last 15 years, you've lost a lot of time invested. Whereas with the JVM ecosystem, similar to the *nix ecosystem, everything you learn retains value. And the JVM ecosystem just evolves around problems and grows even more--whole branches don't go extinct as with the Microsoft / .NET ecosystem.