I motocross raced a 88 Honda CR250 in my younger years, and now a '99 CR250
I road race when there are no motocross races a '00 Honda 929 RR
I've ownded a '73 Cuda with a 383 I stroked to 426 cubes using a 440 crank, about 450 hp
I then owned a '88 Mustang 5.0 modified for raod racing with a full Griggs Racing suspension, nearly stock motor
Now I've taken up offraoding jeeps for fun when I'm not running one of the two bikes, and sold the cars due to tickets

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As for running a motor hot / cold, this is Canada! You can always get more power from a motor cold if it's jetted right, and the motor was built for it! Yes you are very right in saying that the pistons expand, but if you size them right, and never run them hot, colder is better. The air charge is denser and will burn the same if jetted right. Motocross bikes aren't allowed 30 seconds to heat up before the start of a race even at 0c.