First of all, technically, Gandalf was not slain, sorry, I had to.
I do not think the company would have been successful. Gollum was actually the destroyer of the ring and if the company had kept going, I bet Gollum would have been slain.
I also don't think that Gandalf would have chosen the way to go that Frodo and Sam ended up going and it ended up being a pretty easy way to destroy the ring once they finished the Orc march.
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'The Black Rider flung back his hood, and behold! he had a kingly crown; and yet upon no head visible was it set. The red fires shone between it and the mantled shoulders vast and dark.'
Witch King of Angmar as described at the Siege of Gondor
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