Welcome to the group. Does your bike have a serial number (located under the neck, just in front of the crash bars)? There are several guys who opt for the honda (or honda clone) motors & they seem to work out well. I would thing the 19" wheels would look out of place on the Simplex chassis, but I wonder if a guy could re-spoke the honda hubs into the Simplex rims (the width might be too much?). Don't give up on the simplex wheels if they are useable. The 2" wide rims (depending on what year you have.....if it's an early bike, it might have narrow rims) are hard to come by & somebody here will want them if you want to get rid of them. New spokes are available to fit the original rims to the original hubs.
Is your large pulley the bolt on kind, or is it made to clip over the edge of the rim?
An electric bike is an interesting idea.....I've seen a few electric motorcycles sell on ebay, but have never seen one in real life to know how well they get along.
As you've probably seen from the photos on the site, the original path of power is from the right side of the engine, thru the jackshaft transmission, to the output pulley on the left side of the bike (early Simplexes, that were direct drive, were all on the right side). Since the bikes are fairly semetrical, you can go with what ever power train you come up with. The notch for the rear fender is the only thing that would need attention if you switch to right side drive.
Good luck,
Mike S