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If apple releases an update you will need to re-jailbreak your device. Make sure there is a jailbreak available before you update your device.
All apps purchased through Cydia can be re-downloaded for free.
Cydia will not automatically download them for you, but you can log into your account and choose the apps you wish to download again.
I hope that helped!
Do you have to re-jailbreak? Do you have to re-purchase the apps through Cydia? Does Cydia know which ones you've downloaded and automatically download them again?