Having three 285's to clamp, diffuse, trigger/test, and finally meter might be more portable, but not be any easier to set up or fiddle with. You'll probably spend more time checking and replacing batteries. And you don't have modelling lamps to help you see what you're going to get, so I don't like the sound of it at all. I agree with you on umbrellas over softboxes for easy setup, but my gut says one monolight (with modelling lamp) and one reflector. But keep in mind I'm speaking from the school of really lazy.