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Originally Posted by narfforc
If Gollum had found Bilbo, and murdering him took the Ring, Sauron knew that Gollum was already under the power of the Ring and would not be able to resist putting it on. Once Gollum had the Ring, it would be far easier to detect and catch him
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I think nafforc is on the ball here...first of all, I believe that Sauron knew nothing of hobbits and the Shire, so as far as he was concerned, they might have been in league with the Wizzards and the elves, and perhaps they were all waiting for the right time to start using the ring. Of course, the right time for them would have been a bad time for Sauron.
We know that no-one but Gandalf might have defeated Sauron while using the Ring but... did Sauron know this? perhaps he feared that, if given time, they'd manage to overthrow him. Same principle why he actually attacked the Captains of the West when they marched to Mordor with ALL his might rather than a sufficient amount. If he had left some orcs behind, he would have caught Frodo and we can guess what happens next.
So perhaps, knowing that Gollum would use the ring as soon as he got it, Sauron let him go free in hopes that he'd somehow manage to find The Shire, get the ring and use it... thus revealing where the ring is to his minions.
Keep in mind that in Sauron's mind it was a win-win situation, as mentioned before. Pitty was not something very likely in him, nor the desire for something other than power... thus Gollum, a wounded beast that was far beyond healing, had some upside and no downside... if Sauron couldn't think that they'd try to destroy the Ring, then how could he think that Gollum might be of assistance on that same quest he cannot imagine?