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1. You will only lose applications/files that you install yourself, the OS and manufacturer installed applications will remain.
2. Through syncing, no. You might want to invest in backup software like Sprite Backup for this purpose.
3. Installing to different media (like LooxStore or SD card) will ensure that you don't lose your software - but you will lose things like settings, configuration and registration information, in which case you might as well re-install anyway.
4. You can do this on the PDA, or in Outlook if you are syncing with a PC. If you have problems with duplicate entries, I would suggest getting a Outlook duplicate remover (try a Google search)
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"A planner is a gentle man, with neither sword nor pistol.
He walks along most daintily, because his balls are crystal."
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