It's a pain, still. I don't generate js files. When something like that happens, I have to go back to command-line, type 'coffee ...coffee', open generated js file and see where the problem was.
That's your problem right there ;) When you're using CoffeeScript, you're absolutely supposed to generate all of your JS files. -- For the same reason why you don't run all of your JavaScript via eval() while you're developing.
OK then. I have already 7-8 tabs in my terminal open all the time (a few for servers, some for redis, some for mongod, some for vi, some for other tools, some for debugging, etc.), so I guess another tab wouldn't hurt (I'm not a fan of running processes in the background).