A future OS update can break app compatibility if the app is not updated, apps not on the store won't be updated
Restoring a device from cloud backup will download all your apps, except apps no longer on the store
The device right now, with the OS right now, with the app right now will still be able to use this app and its file sharing feature in perpetuity which is an aspect that isn't different or worse than other kinds of devices or computers. Only the system restore embellishments being different or better or worse. People on other systems that pay for apps can still run into scenarios where their updated operating system is not compatible with an app they paid for. I'm not trying to be an apologist for things Apple or the mobile landscape could do better, only pointing out the standard people seem to be asking for without realizing it.
