How to get meniscus down to the calibration mark with a volumetric pipette
If you have to stopper the pipette with your finger, it just takes practice. I believe the proper way to do it is to just roll your finger to the side very slowly, but I've heard several strategies including rotating the pipette like you said, and rocking/sliding your finger back and forth.

It is a lot easier if you have access to pipette bulbs like these, which let you squeeze the side arm to expel liquid smoothly:



These are easy to use too - you just roll it down to expel the liquid:



Most labs should have either of these, especially university ones. Maybe less common in high schools.