When the wheels go up
Scores should erupt
But they’ll say I’m a clown
If they don’t come down
If the judges were managing to be completely objective, retracts would only make a difference in as much as they affect the aerodynamics of flight (and if they make it worse -- oops). I suspect that if you get any points from the "wow" factor, it'll wear off as the judges get used to seeing the wheels go up.
I'm sure you're already thinking about this, but it sure seems that you'd want to think carefully about when you want the gear to go up. Too soon and the "wow" factor is of entirely the wrong kind. Too late and you don't get nearly as much "wow" as you'd like. Just right, from a purely aesthetic point of view, would be to start a slow retract right as the wheels leave the ground -- but that really flirts with 'too soon' if anything delays takeoff.
I'd be concerned with the retracts messing up the airflow when I'm trying to achieve a smooth takeoff and level flight (actually, I'm a rank beginner -- I can't reliably achieve level flight yet, so retracts would just give me something to blame other than myself). At worst, you could time things so that the wheels went up after your two laps of level flight, but that would certainly remove a lot of the "wow". At best, any bobbles from the wheels going up would be slow, and could be timed for the climb phase of the takeoff where they'd hopefully get subsumed in the overall climb.