In my experience it's always best to restore to stock firmware before jailbreaking.
Also, I always setup my iPhone as new in iTunes when I'm finished with the jailbreak. Then, I just sync my contacts, calendar, photo's, music, apps, etc. back in to my iPhone. I never restore from a previous backup.
I've always come across a problem or two when restoring from a backup or not doing a stock restore before jailbreaking. But other people may have had success.
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White iPhone 3GS 32GB
Firmware 3.1.2 jailbroken with Pwnagetool 3.1.4 on my PC running OS X Leopard & Windows 7 Ultimate!
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