[Silhouette]

But in the long run, I'd rather pay, say, $20/year for a useful piece of software in perpetuity than $100 once every five years--because that way I always have the latest version and don't have to think about whether I really want to upgrade or not. And that aligns my incentives with those of the developer and reduces their support costs.

Someone in my household got prompted to upgrade an iOS app they enjoy this evening. Apparently in this case, that person's incentives were aligned with the developer's, except for the new version including ads that weren't there before, charging via IAP for content that was free before, and not actually running anyway because it now has iOS 9 as a minimum requirement.

Sometimes having the latest version is a double-edged sword. If the developer has no incentive not to exploit customers who are already locked into their subscription model anyway, make that most times, in my experience.