key command to turn ON Transport Cycle ( not toggle)

I don’t think there is any way to make this work in a toggle-only world.

The only approach I can think of is to create 2 Macros, one that toggles the loop & one that doesn’t. If you assign each to a key then you could decide which to use based on the current loop state. So it would be one keystroke, but you’d need to choose between two possible keystrokes.