Regarding the apportioning of the Land under the auspices of Moshiach, there are two things to remember. First, the ultimate delineation of the Land is clearly spelled out in the final perek of Yechezkel, so we know which Tribe will be situated where. Second, navuah will return with rebuilding of the Bais HaMikdash, if not sooner given the right circumstances. With that, it will not be a problem to understand the specifics of Yechezkel, or to ascertain who the original owners were of which plot of land and who their descendants are; subsequent land sales would certainly be handled in the appropriate manner. That might not be how things are handled when the time comes, but it will be possible to do.
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