I use "whilst" from time to time. Although according to the link below, I may be using it incorrectly:
http://dictionary.reference.com/browse/whilst
I'd let out the clutch in 3rd or 4th when bump starting. As soon as it starts to fire, push in the clutch to let it up to idle speed.
I wonder if your igntion timing was advanced enough it put extra stress on the starter. Mine was too advanced for a while, and I think that's why the nose-end bushing shifted out of position causing the armature to drag.
I use a long wrench to move crank to timing marks. If I was to use a remote switch, I'd put it in the low current terminal on the solenoid....same one the ignition switch provides power to. I'm not comfortable with a portable switch handling over 300 amps. Not sure where you put the switch, but just in case.....