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I don't think it would be impossible. Extraordinarily difficult, yes. Impossible, no. Some places would be easier than others. The Shire probably wouldn't be all that hard. Someplace such as Gondor where all the people are spread out would be more difficult. Another place worth mentioning would be the area of the Grey Havens. There were quite a few Elves living there still.
As for estimating, I will use Rohan as an example. At the time of the WotR, they sent about 6,000 men to Gondor and still had some left to guard the country. I will say they had about 8,000 men total. Then there were probably about the same number of women, maybe more since they don't fight in battles, etc. So maybe 8,500 women. That's 16,500 people. Plus the children and the elderly, which would probably be slightly less than the totals of men and women. I'd say you are probably looking at a few more than 20,000 people in Rohan, which really isn't all that much.
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