In the end, I probably would have paid the full price for the new version even though it’s really only a re-skin of the old version. But I still applaud their cleverness. They’ve given their customers a way to feel good about an upgrade and apparently found a way to do it without relying on typical IAP unlocks to power their business.
My understanding is that the app comes with three separate In-App Purchases: two for a discounted upgrade, and one for people who don’t have previous versions of the app installed. If old versions are recognized by the app on the same device, the discounted upgrade IAP is activated; otherwise, the app only shows the full-price, $9.99 IAP to “unlock” the new app.
It’s not exactly a straightforward process and I’m not sure that Apple is a fan of the idea of having a standalone “Upgrade” app, but it’s clever considering the App Store’s limitations. I’d be curious to know how well this goes for Headlight Software.