From my point of view (I don't know the architecture of the app) it shouldn't be problematic so much. My two check-items could be rewritten in the programmer's language (probably) this way:
JobScheduler- it doesn't matter if the whole service will be down or if it checks every 15 minutes if is enabled (and then do the job as today) or not (sleep again)
- call the function
tryToUploadWhatWasNotSentYet(sorry, don't know the exact name) which is called by the
JobSchedulerevery 15 minutes
The calendar thing could be only extended function of "enable/disable". In other words - enable again at a specific time.
Sorry if I'm completely wrong due to misunderstanding the current project structure.
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