Good guys of LOTR clueless?

[The Saucepan Man]

Oh please. You're calling Sauron "not very bright"?

I certainly would not describe Sauron as thick. But there was a very significant defect in his intellect, and that was his inability to understand humility and sacrifice. For him, the desire for power was so great that he could not imagine that anyone, faced with the means of obtaining it in great measure, would not feel the same desire. Only at the end does he realise his folly. And that word, which is used in the passage from which your original quote comes, is a most appropriate one. For all his intelligence, he nevertheless showed great folly in severely underestimating the capacity of his opponents (particularly Gandalf and the Hobbits) to show great humility in the face of the opportunity to obtain great power.

Well, I figured this theory would seem too anti-good guy to fly with most, but I'm surprised that there hasn't been anyone at all on the Downs that is willing to play along a bit and maybe has some thoughts or quotes that would go with it.

Sorry, I would love to if I could. But by no means were the good guys clueless. All they could do was act on the information that they had at any given time, which was necessarily incomplete.

And neither was Sauron clueless. As has been said, despite imbuing the Ring with part of his own will, he had no way of knowing exactly what would happen if it were to be destroyed. Indeed, the Ring almost certainly didn't know itself (although obviously it was keen to prevent this situation occurring). Again, he could only act on the information available to him at any given time, although, in Sauron's case, his actions were constrained by his blind-spot when it came to assessing the motives and qualities of his opponents.