Concerning the initial question, I would also note that in letter #181 Tolkien excludes pretty much any merit Gollum could have:
Quote:
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Gollum was pitiable, but he ended in persistent wickedness, and the fact that this worked good was no credit to him. His marvellous courage and endurance, as great as Frodo and Sam's or greater, being devoted to evil was portentous, but not honourable.
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