At the core his point strikes me as inane - that he won't spend a tiny fraction of the cost of his other equipment to solve a problem, that he clearly underprices his time - but still, the pricing strategy here sounds flawed.
I use Synergy, too; I'm all Windows so Mac-compatibility isn't an issue, but it's a nice program. Note nice though. Not deal-breaker, not revolutionary, not transformative. Could I be persuaded to pay for a better version? Sure, but only so much. Elasticity of demand as highlighted in the article only goes so far; ultimately there will be a ceiling price above which your revenue falls.
It's a gadget, not a core tool, and (IMHO) needs to be priced at the 'impulse buy' level. $25 / machine is enough to make people think (even if it's a tiny fraction of total system cost) and you're suddenly out of impulse and into avoidance.