Whoa! According to Pio's map (or whoever's), the Shire goes farther north than I was thinking. In fact, I'd prefer to take issue with that map and say that the Shire shouldn't go that far north. That's not at all the way I ever imagined it. Did you? Long Cleeve seems way too far north to me. I had the Shire's northern border at the southern edge of those hills south of Lake Evendim.
At any rate, for the sake of the rpg, Eodwine can be understood to have come first from Buckland, then to Bree and The Prancing Pony, and then north (not directly by road), captured just a hill or two south of the "caves".
If we accept this map, then the outposts of our evil nemesis will have to be on the north side of Lake Evendim, since the south shore IS the border of the Shire, and the villain-in-charge is too smart to mess with the Shire directly - yet. He knows well what happened to Sharkey there.
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