I love against the grain thinking, thanks for sharing, and for sharing how the big companies do it. 
You mentioned about getting to the retargeting idea, but never really addressed it. What’s your take on paying for freebie seekers and pixeling them? How do the numbers stack up?
And also, the numbers with squeeze page dont work for one offs. What’s your take for a membership/recurring setup where the “upsell” product is a recurring $47 or $37. As it’s recurring, the cost will eventually make sense. What’s your take on recurring products?