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Another work-around I've seen is updating the old app that has a one-time popup to alert users to the new version. As a user, I can live with that as long as it is a one-time popup.

This is really something the store should handle.

Notifying users is the easy part. The hard part is offering upgrade pricing, rather than forcing users to buy the new version at full price.

I think I've seen a workaround of offering the old and new versions as a bundle? That's pretty ugly, though.

That's a janky workaround. You have support both the old and new features/behaviors in one app, and push an update that wraps the old and new features in code like 'if(IAP_X_ENABLED())'.

Any architectural refactorings aren't compatible with that model, so you'd have to launch MyApp2019 and MyApp2020, and hope Apple lets you do that.

You can use IAP for upgrades. it’s just a bit more work, grows your testing matrix significantly and is a bit more confusing to your customers.