It helps to be literal here: dose arithmetic has three parts: concentration from vial content and diluent, volume from dose and concentration, and units from volume and syringe scale.
Number of stopper piercings matters less than the gauge doing the piercing. A 30G or 31G needle through a butyl stopper leaves a track that reseals; a 21G or 18G drawing needle punches a core and can drop it into the solution.
Room temperature before drawing is worth the ten minutes. Cold solution is more viscous, draws slower, and condensation on a cold barrel makes it harder to read the meniscus.
The insulin-unit standard U-100 means 100 units per millilitre, so one unit is 0.01 mL — this is the conversion that trips up more people here than any other single piece of arithmetic.
One qualification: if your arithmetic and someone else's disagree by a factor of ten, one of you has made a unit error, and writing out the units at every step is the diagnostic.
Write the arithmetic on the vial label. It costs nothing and removes the step where you reconstruct it from memory.