#5 could be MELKOR (reversed); he was certainly ahead of the other Ainur, and loved singing his own solo, and his name literally means 'he who arises in Might'.
Alternately, the geographical theme we seem to be wandering towards could indicate LAMMOTH, the valley holding the echo of his great cry. It would probably still be reversed.
Edit: incredibly cheeky answer to #1 - if we accept Tom Bombadil as the 'incarnation of the One (=solitary)', then he did indeed live in what Frodo called 'the shadowed land'... making the answer OLD FOREST.
hS