Is #5
OLD MAN WILLOW? 'Senior citizen' + [weeping] willow, plus he was embarassingly outsung by Tom Bom Jolly Tom Tom Bombadillo.
And if we're doing stab-in-the-dark guesses at the password... NIMLOTH would fit, and would keep to the 'tree' theme.
(I have been driving myself crazy staring at the list of Numenorean tree species, just so you know.)
EDIT: So, for #1...
NISIMALDAR, the Numenorean land of fragrant trees, can be broken up as LADS + MARINI. 'Lads' as in boys, and 'marin' is French for sailor. 'Marini' isn't a French plural, but it could be a Quenya one (of a French word)...
EDIT 2: And #4 must be
LEBETHRON, the wood used to make walking sticks for Frodo and Sam, and also (apparently) to carry the Crown of Gondor. It was definitely carved up, but I feel there's an anagram in there that I'm not seeing... unless 'high and honorable' is referring to the theory that
Lebethron is the Entwives?
hS