Siphoning problem, ruined?

The volume of air entering the stream during the first couple of three short pumping strokes is trivial.

 

That's possibly true. But the OP's concern was about doing many pumps.

 

A good trick is to "prime" the siphon with star san solution, by pumping the solution from an extra bucket into an empty gallon jug. Once you get a good siphon going with the sanitized solution, use your thumb to block the out flow, and transfer the siphon into your primary. No pumping required if done correctly.

 

yes, but I only do that right before I bottle. It doesn't stay in there for weeks on end. Not that nylon paint bags are an inherent problem though.