Fwiw we have remote debugging to any OS, so you can remote debug your app regardless of whether or not it's running on azure. We are striving to streamline this experience as much as possible, so any feedback or ideas you have on how to mitigate some of windows issues you've run into would be super helpful. :-)

The two major issues I have run into with doing node on Windows are likely out of your control. First is the file path length limitation, which conflicts with the nesting of npm dependencies. Second is dealing with any packages that depend on node-gyp for compilation. It shouldn't require an entire IDE to be installed in production just to build your dependencies that need node-gyp compilation. Not to mention that the process is problematic even in dev if you're not lucky enough to have installed the exact expected dependencies. I found it easier (and more portable) to just use a VM running some *nix flavor (Ubuntu for me) and deploy to a similar environment.