Welcome to the wonderful world of boating! Pulling the boat out with the motor running is a new one, never heard that one before. Fortunately you don't have to worry about launching with the bilge plug out, pontoons don't have one. Also, if you leave the outboard down you usually won't grind down the skeg (fin) on the engine, 'toons sit higher on the trailer and won't drag.
I'll bet you will:
Try and launch with the tie downs attached In back (done it several times)
Launch with the transom saver still attached (Only once.... so far)
Launch with the boat ignition keys in the car..... that just pulled up the ramp to the parking area (once)
Shall I continue, or wait until you and everyone else stops laughing...... you all know you've done it too!!!