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@NurseHolliday
No. If your iPhone has previously been synced with your iTunes it will have a backup. When you restore it will ask you if you want to put the contents of that backup onto the newly restored iPhone you have connected.
Also, Jailbreaking has no software update problems as long as you set your update option to notify you of an update, but do not auto install. That's when you get a bricked iPhone.