A fan like you are talking about might be able to push someone on a bicycle a few MPH, but lets say the fan makes a 10mph breeze, if it's behind a vehicle that is going faster then the breeze from the fan is still drag.
The fan also creates turbulence that slow both the fan and the vehicle down, so depending on placement, there is a chance that the fan just being turned on is going to slow the lead vehicle down more then it being turned off.
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