Who wore the brooch?

Those princes used to have many wars against each others and most probably Tom could not understand mens desire to possess and rule. Mayby he remebered her, innocent women who was slaugtered because of useless urge to possess, and Tom remebred her and decided it was a worthy gift.

Still, no elven I think.

It seem to be wholly overlooked, apart from the side-note by Tolkien.

A part of the Dúnedain of Cardolan most probably would have merged themselves with their counterparts in Arthedain, (note 'faithful Dúnedain' some may have switched sides, such treacheries have happened before, as Elrond states) and some of them may have eventually left the Old Forest to join their counterparts in Lindon.

And though Angmar was subdued by Elves from Lindon, Lothlórien and Rivendell but during the reign of Argeleb II (Araphor's son) the great plague had ravaged the remnants of the Dúnedain of Cardolan.

Major deforestation? Given the aggressive nature of the trees in the old forest and their possible friendship with Bombadil it is doubtful as to whether they would or would need to deforest the Old Forest. Although the Northmen de-forested a lot of Eastern Mirkwood (East Bight) a lot of men could live in forests without the need to deforest them.

Khazad-Bombadil seems to understand Old Man Willow's purpouse's pretty well.

Oh yes he can understand it. My meaning was that Tom did not have those desires, that does not rule out he could not understand them. Hmmm, have to write more clearly.

This may be a little off-topic, but I have decided to draw and colour my representation of this jewelled brooch that Tom finds.. I haven't even started it yet though, and it'll take a while because I have other stuff to do..
Just thought I'd let you know. I'll put a link here when it's done and uploaded.

I love to see that!