This is arithmetic, so let us do the arithmetic rather than argue about it.
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.
Worth being precise here: air bubbles at these volumes are a measurement problem rather than a safety one. A 2 mm bubble in a 0.3 mL syringe is roughly 4 µL, which at 10 units drawn is a four per cent error.
The limitation is that technique reduces risk, it does not remove it, and nothing you can do outside a controlled environment makes a non-sterile preparation sterile.
Do the arithmetic twice, ideally with someone else doing it independently.
edited 5 Mar 2025 by pascal_thibault — fixed an arithmetic slip in the third paragraph