Recently I started digging how one could write a debugger for VS, and integration for a language (dynamic one). I stared by looking at pytools, and I was confused by all COM objects, classes, etc. I was not sure at what I point I'll get it to work - do I press F5, and it's installed? Do I make a DLL and it has to be registered?
Now that other plugins are easier - I'm looking now at MonoDevelop and SharpDevelop (Windows Only) but I wish something simpler - like emacs - straight to the core of the system - functions exposed, communication channels right there for you, etc.
Anyway I won't give up, it's just taking too much of my free time.