I have a friend with a iPhone 3gs purchased in America over 2 years ago and never updated and it is on ios4! Over time the phone has gotten slow and not running to its fully potential
With recent developments in jailbreaking and unlocking its is in theory for him with his baseband to update to ios5 and jailbreak through the new ultras 0w update as his BB is listed and supported!*
As American phone and no idea of sim to activate and possible not being able to use the phone would you risk trying to fix the phone and updating to iOS 5?
And if so what jailbreaking processes and software is best advised?*
There is little risk in buying it as you will always be able to unlock it with the ipad baseband (though GPS may not work).
I would check the baseband and see if it will be unlockable with ultrasn0w, then do a custom firmware with pwnagetool to 5.0.1 and unlock. I think this would work only up to 4.0.1 from memory.