Well Samwise, the thing with Gollum searching was that he tried to let the ring go, even though he couldn't. He couldn't because as you said, he went to great lengths looking for his precious. And he got more desperate the closer they got to Mt. Doom. However, the reason I say that he was trying to quit was because he had a chance to take it, but chose not to. Many times he could have done away with Sam and Frodo and taken the ring. Like at Ithilien. Gollum is very cunning and crafty. He could have strangled Sam first, or came up with another way of ending his life, while Frodo was separated from him. And then Gollum could have killed Frodo and taken the ring. Do you recall the steps at Cirith Ungol? When it said
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Gollum looked at them. A strange expresssion passed over his lean hungry face. The gleam faded from his eyes, and they went dim and grey, old and tired. A spasm of pain seemed to twist him, and he turned away, peering back up towards the pass , shaking his head as in some interior debate. Then he came back, and slowly putting out a trembling hand, very cautiously he touched Frodo's knee-but alost the touch was a caress. For a fleeting moment, could one of the sleepers have seen him, they would have thought that they beheld an old weary hobbit, shrunken by the years that had carried hmi far beyond his time, beyond friends and kin, and the fields and streams of youth, an old starved pitiable thing.
But at that touch Frodo stirred and cried out in his sleep, and immediately Sam was wide awake. The first thing he saw was Gollum-'pawing at master,' as he thought.
'Hey you!' he said roughly. 'What are you up to?'
'Nothing, hothing,' said Gollum softly. 'Nice Master!'
'I daresay,' said Sam. 'But where have you been to-sneaking off and sneaking back, you old villian?'
Gollum withdrew hmiself, and a green light flickered under his heavy lids. Almost spider-like he looked now, crouched back on his bent limbs, with his protruding eyes. The fleeting moment had passed, beyond recall.
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I strongly believe that Gollum was debating whether he should really take them to Shelob or not. Smeagol was fighting the addiction of the ring right there. He was wieghing the worth of his drug, the ring versus the power of friends, acceptance, love, compassion, etc., which he had not been offered in over 500 years. And he found that friends and the other stuff was more important than having the ring. His battle was was hard fought and well deserved. It was a major step forward in the right direction. But then because of Sam, he was knocked backed 5 steps in the opposite direction; too far to ever recover from.