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I don't think it would entice more people into upgrading. People don't necessary want to stay on old versions, they just don't want to be interrupted.It might, if you did it like GP posted:
>> a little note pops up informing me that there's a bug in sorting non-ascii characters that was fixed recently
>> The program downloads the changelogs in the background (if the user chooses)
Note the stark deviation from standard practice: GP would like the popups to actually tell you what's in the update.
In my experience with both techies and non-techies alike, the main reason everyone hates updates is that it's always a cat in a bag. You'll likely get some bug fixes. You may get some new features. Some of those may even be useful. It's more likely the app will become slower instead of faster. It's quite likely there will be disruptive UI changes. Often completely gratuitous ones.
Random recent example: I noticed my wife has an OS update on her phone pending for the past three months. I asked, she agreed, I did the update round. Told her, "wow, you're getting a version bump, I envy you". I immediately noticed some user-set icons were wrong[0], but quickly corrected it without saying anything. I though that's the worst of it. Couple hours later, she comes back to me complaining that the update messed up notification sounds and the new keyboard has changed scaling, breaking her muscle memory for touch typing. Also the battery life dropped significantly.
Updates today are like loot boxes in games, except most of the "rewards" make your life worse.
One solution to this problem would be to have a separate stream for feature updates, and a separate one for bugfixes and security updates - and only ever bother the user about the latter. But that would increase the costs for the software vendor, and we can't have that. Who are you, the user, to complain about what your lord does? SaaS stands for Serfdom as a Service.
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[0] - The ones you assign to your SIM cards in dual-SIM use scenario. The update added new icons to the set, and apparently the OS must have been storing user choice as an index into that set, instead of using icon ID.