Yes the problem is that the electric drill has no "feel" you can normally feel the rubber getting tight when things are close to the max when you use a hand winder.
The wider the rubber the more the power... 3/16" rubber will be fine in this model, at least for a start
The choice is yours of course, but I'd go for the 10:1 winder, the maths is easier!!!!!
The winder will of course let you stretch wind, which will give you more winds. (remember those pictures I posted of my FROG model?)