I'm just conjecturing, but wouldn't it be possible that Old Man Willow is one the trees that act more like Ents that Treebeard mentioned. And if that's so, it could make sense for him to be bitter. As he awakened, he had no guidance from Ents, and in his intellectual solitude amongst a bunch of trees, he would naturally become bitter over that ages.
And about Farmer Maggot visiting Tom Bombadil, he probably went the long way around the Old Forest, cutting through the Barrow Downs instead to reach Tom.
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"Come away! Let the cowards keep this city!"
-- Fëanor to the Noldor
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