The latest version of Bento for iPad is out and it reveals how Apple may approach paid upgrades in the App Store. Bento 4 1 is currently on sale for $5. That's a good price. But Apple is showing how they want paid upgrades to function. They removed the previous version of Bento from the App Store and replaced it with Bento 4 as a new purchase.
I say "Apple", because FileMaker Inc. is an Apple subsidiary. I don't claim to know how Apple is structured, but they do appear to operate as a cohesive entity. That leads me to the conclusion that Apple is endorsing this model of paid upgrades. It's probably the future of many more apps as the App Store ages. I'm ok with this model though. The pricing of these apps is low enough that I no longer expect a single purchase to continue to receive updates indefinitely. When an application cost $60 I expected for it to last longer. At $5 or $10 dollars, I have lower expectations for long term support.
Unfortunately the cutover can be a bit rough:
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