I know that you can continue to sync with iTunes after jailbreaking, which means that iTunes should still be up to date with all of the photos, apps, contacts, etc that you have added to your phone while jailbroken.
If/when you wanted to restore your phone to 'factory' condition after a jailbreak however, would doing so revert it back to the point in time right before the initial jailbreak or would it restore it but still keep the latest information? I know you go in and choose the IPSW file when you do the restore, so I just want to confirm that that particular files get updated with each subsequent sync.
I hope that makes sense. I basically just want to make sure that I wouldn't lose all of the information I've added to my phone over the course of a long time being jailbroken.
You'll restore it to new first and put whichever firmware on you want/need. Then you'll restore to your last backup (when jailbroken). This will restore all your music, pics, contacts, and iTunes apps.