Excellent article, but I think it's important to point out that in both his examples (his own sales and the theater) the products/shows are being compared to products/shows that are vastly more expensive. Even after raising his price, qlab sounds pretty cheap next to other similar programs prices at $1000+. Even if the theater tripled their prices, they'd be pretty cheap compared to broadway.
If the standard price for an audio suite like his was $50, I bet the increase in price to $249 would not have been as warmly received (to put it mildly). I don't think this works if your product isn't comparable to some other product that costs an awful lot more than what your charging.