I'm still not totally understanding your need. It sounds like you might have iFly on a tablet that you leave in your plane, but before you close your flight plan you leave the plane and tablet? You also have iFly on your phone, which perhaps runs as a backup and you take that with you when you leave the plane?
If so, then perhaps iFly could send the "Did you close your flight plan?" message from your in-plane tablet to your iFly phone in the same way that it shares flight plans.