I currently am still running 1.1.4 on my first gen iPhone and love it, have no problems with it. However i would still like to upgrade to the 2.0.2 software that is currently out but would like to keep my phone Jailbroken. Now i know it can be done and you can jailbreak it without a problem, my only question is can i do it and keep everything i already have on my phone on it, or willl the upgrade and then the jailbreak of the 2.0.2 software reset my phone when it creates a new ispw.
Is there a way to upgrade and jailbreak without resetting all the info, apps, contacts etc that are all already saved to my phone?
You will lose everything but the sync will put it back on. As for the apps (from installer or cydia) they will not work. A good part of them have been updated for the 2.X firmware so there is a good chance that you will find it in cydia. My suggestion is make sure you do a sync before upgrading. This will ensure that once the 2.0.2 has been successfully installed, you will be able to restore from backup.
I've had problems with syncing a backup from a custom firmware. For example, I can backup continously with no problems but once I upgrade or do a restore, the sync will be me an error. I've heard others have this problem as well so I'd keep that in consideration.