It looks darned clever to me! I tried to make my clues hard because the standard I found here was so high. (I was completely at sea on the Ossiriand and Amdran (is that right?) clues).
I also have a Daily Mail book of cryptic crosswords by my bed that I am gradually getting better at - but I still have to look up the answers in the back quite a lot!
I think there is truth I Gandalf's observation that shared origins are a help when it comes to solving riddles...more likely to get the cultural refs and knoww the same clue conventions.
I wonder if that was why I didn't get the "letters" thing in Galadriel's Ossiriand - or is that more to do with being used within a particular profession?
P.S. No, I can't solve this clue. Not yet, anyway.
P.P.S. Sam would probably throw apples at me for forgetting Bob.