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The main landing gear themselves create lots of drag, because during retraction it rotates and the wheels turn into a barn door.
For me, I don't care about the end of the runway -- you'll never stop by the end of it if you've already lifted off, unless the runway is 10,000ft plus. So, when I climb out I check airspeed, climb rate, and most importantly both engines. Then I raise the gear. With two engines running the gear drag isn't that big of a deal. However, when taking off on a hot summers day from Albuquerque, the airplane will level off. So under high DA conditions I tend to climb much higher first before brining the gear up.
None the less, your CFI isn't doing you any favors -- unless you are flying a Barron.
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