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Okay, so: for the first W, could this be WELLINGHALL? Meduseld is the Golden Hall, and a water-meadow might have water welling up?
For H: HITHLAIN is the material of Lorien cloaks, and sounds like 'He's lain'.
Of the remaining 4 clues, it looks like we have one object (O) and three places (T, T, W). No people, which is nice to avoid random Riders. So I'm just going to throw out some thoughts for now:
T(1): Who complains while fasting? Hobbits, including Gollum.
T(2): I... don't even know where to start.
W: How many flippin' places beginning with W can there be? Most of them start with 'White'. 'Desire' suggests a name starting with WANT, but... there aren't any. Could be Want + He[something], so that 'the' can be removed from the middle, but what's the something?
Or, this could be just a big long straight clue, and point at the WINDING STAIR as the place where Gollum had his final turn back to evil.
hS
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