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Your CFI is half right about raising the gear. In fact gear down does very little to detract from cruise speed in a skymaster. However you can adjust your speed at takeoff by merely changing your pitch. Your bigger concern is Rate of Climb. In that area, the cycling of the gear doors is of vital importance shortly after takeoff.
Keep your gear down until 500 feet AGL and it is one less thing you have to think about in case of emergency, and eliminates the gear door drag on every takeoff/inital climb out
Speed is of course more crucial on takoff than altitude (after all you don't stall a plane due to altitude, you stall due to too low of airspeed) but the difference with the gear down is so slight, it isn't worth sacrificing the negative side of the gear cycle, for the 1-2 knots the gear itself is subtracting from your ROC.
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