Out of curiousity icey, where would these languages fall on your chart:
ruby on rails?
scala?
python?
I'm attempting to "download" web programming languages in an exceptionally short time but I'd prefer focusing on high end producers. I can see advantages and pains to various syntax and functionality, and have been fairly liberal in my choices so far to focus on existing libraries.
For me, they're different 'flavours' of programming and fit on a different chart. The C++/Java/C# line is for static programming with heavy reliance on a compiler -- the idea is that the compiler helps you find lots of errors. In all three languages, getting the program to compile rules out whole rafts of problems.
Python and Ruby move that responsibility onto tests -- you run the code to find errors.
I think C++/Java/C# fit onto a line, each taking away accidental complexity and adding higher level features. C# iterators and lambdas are a good example the OP mentions, of a high-level feature that makes possible styles not available in Java and C++. (we use C# iterators and lambdas to write in a more functional style than we could in Java)
My "daily drivers" are C# and Python. I'm picking up Clojure right now, but haven't really done much with it - I really like lisps in general, but for some reason always fall back to either C# or Python when I need to write something I'm going to maintain.
If I were in your shoes, I would start with Python and Django. It's a good framework on a good language, and most importantly, Django has a very good community and almost peerless documentation that's available for free online.
Ruby on Rails is also quite nice, I'm just not a big Ruby fan. There is no reason for this other than personal preference. Scala seems very interesting, but I personally don't see a gain in learning it (since I have C# in my toolbox). Your mileage may vary.
For whatever it's worth, everyone I've dealt with seems to have had a pretty painless transition from C++ to C#. I am not a Java person, so I can't really speak to that.
