I told my boss that I had done capacity planning and that the $9 a month quota was sufficient to our needs. "Nice job, Patrick. I am not putting Hobbyist on any piece of paper that I have to show *my* boss." Not first nor last company to spend $20k to avoid an eyebrow raised.
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The incentive for the end-of-year promotion email is (for relatively small businesses) booking the expense before end of year saves them a bit of money on taxes and (for relatively more sophisticated businesses) "Your budget: use it or lose it. Why not use it?"
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"Patrick, are you assisting people in defeating their purchasing departments?" *cough* Never. *cough* Really: $249/$499 exist as price points specifically to do security research about the bounds for no-signature-required p-card limits while allowing $10k+ software sales.
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(In related news, enterprise purchasing departments and enterprise sales are basically in an uneasy state of codependent evolution with each other. Their iterated game is ultimately prosocial, and neither can exist without the other, but they have to be tactically adversarial.)
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