[ROTB]

I am currently evenly split between C++, and Python.

Please correct my bad assumptions, and make sure I have analyzed this problem correctly. I don't want to re-start once I start.

Perhaps when I am done writing it in Python, "Shed-Skin" would be mature enough to use. Risky!

[krb]

Personally I like Python with wx.Python for GUI stuff. Runs on Windows, MAC, and Linux just fine.

[cynwoody]

See if you can write your app in Ruby. It's really simple. You can write the performance-critical guts of your app in C++ and use the Foreign Function Interface (ffi) to access it without writing tedious glue code. And, if you need the Java libraries, you can seamlessly transition to JRuby and use them without having to get lost in the monumental tedium which is the Java language.

Within the Java orbit, there are also Scala, Clojure, Groovy, and Jython. Scala gives you all the power of Java with a much more powerful syntax. Clojure relaxes the typing constraints without too much sacrifice in performance. Groovy is a scripting language designed to appeal to Java programmers. Jython is a Python on top of the JVM.