Sure it will work, mileage of course is the question.
I think it would be worth while to see if you could find a clutch that would hold up so you could have the engine power the wheels at cruising speed, a light weight motorcycle chain could even be used as your engine shouldn't need to be over 15hp or 20hp, you might even be able to get away with not using a clutch and instead shifting it "in to gear" once the speeds match up, or use a centrifugal clutch on the tail shaft of a motor that has a tail shaft so once you hit 60mph say, the motor generator lock together powering the wheels directly.
You'll also need a battery bank to buffer, unless of course you over size the generator or are willing to wait for train like acceleration, 0-60 time of 20 minutes?
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