You can already send different messages for one press, and double presses (double trig in the Editor).
As for the LEDs, if all you're looking to do is reflect the state of a Looper via the LEDs it would be more practical to setup a M4L device that monitors the Looper, and sends the proper MIDI message to the SS to control LED state (which I have setup for people a few times).
that being said, you COULD set up a modline like this to kind of get what you're after.
I say kind of because I doubt that the internal state of this modline will match up with the state of the looper at all times. That's why I suggest tying the LED behavior directly to the looper state. If you don't do that it's easy to get the two separate logic structures to remain in sync.