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Instead of using a chain drive, you might consider using timing belt pulleys. V-belts need a bit of tension and rely only on friction, while the timing belt has the teeth to help with grip. Just thinking a gear reduction using a cam pulley on the motor and the crank pulley on the output would give you a good, reliable, quiet and maintenance free gear reduction and would weigh a bit less. Lots of cruisers use a timing belt arrangement as their main drive.
How much drive capacity you expect to lose without the regen braking?
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