Hmmm, my map in the Fonstad Atlas shows the northern borders of the Shire indeed exceeding Long Cleave by a good 20 or so miles. That places it within the southern tip of the Evendim Hills.
Annuminas and Lake Nenuial lies roughly 20 miles north of that border. I think, like you, that the margin is too slim.
However. I do like the ideas you put forward still. So if we put the outpost on the northern shore of the lake, that gives a margin of around 40 or so miles till the northern border of the Shire is reached.
Those are very rough estimates based on a passing glance at an imperial distance scale and a metric ruler.
The revision in outpost location would also add more buffer between the "baddies" and those remnants of Elves that are congregating about the Grey Havens in Mithlond.
So, the revision works for me. At any rate, I imagine the villian would not be too keen to make a camp in the ruins of an ancient foe at Annuminas.
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Characters: Rosmarin: Lady of Cardolan; Lochared: Vagabond of Dunland; Simra: Daughter of Khand; Naiore: Lady of the Sweet Swan; Menecin: Bard of the Singing Seas; Vanwe: Lost Maiden; Ronnan: Lord of Thieves; and, Uien of the Twilight
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